title: Carbon-13 and carbon-14 labeled dabigatran etexilate and tritium labeled dabigatran.
abstract: Dabigatran etexilate or pradaxa, a novel oral anticoagulant, is a reversible, competitive, direct thrombin inhibitor. It is used to prevent strokes in patients with atrial fibrillation and the formation of blood clots in the veins (deep venous thrombosis) in adults who have had an operation to replace a hip or a knee. Pradaxa is the only novel oral anticoagulant available with both proven superiority to warfarin and a specific reversal agent for use in rare emergency situations. The detailed description of the synthesis of carbon-13 and carbon-14 labeled dabigatran etexilate, and tritium labeled dabigatran is described. The synthesis of carbon-13 dabigatran etexilate was accomplished in eight steps and in 6% overall yield starting from aniline-13C6. Ethyl bromoacetate-1-14C was the reagent of choice in the synthesis of carbon-14 labeled dabigatran etexilate in six steps and 17% overall yield. Tritium labeled dabigatran was prepared using either direct tritium incorporation under Crabtree's catalytic conditions or tritium-dehalogenation of a diiodo-precursor of dabigatran.
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA.
authors.forename: Bachir
authors.initials: B
authors.lastname: Latli
authors.affiliation: DMPK, Boehringer Ingelheim Pharma GmbH & Co. KG, Birkendorfer Strasse 65, D-88397, Biberach, Germany.
authors.forename: Ralf
authors.initials: R
authors.lastname: Kiesling
authors.affiliation: DMPK, Boehringer Ingelheim Pharma GmbH & Co. KG, Birkendorfer Strasse 65, D-88397, Biberach, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Aßfalg
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA.
authors.forename: Max
authors.initials: M
authors.lastname: Chevliakov
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA.
authors.forename: Matt
authors.initials: M
authors.lastname: Hrapchak
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA.
authors.forename: Scot
authors.initials: S
authors.lastname: Campbell
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA.
authors.forename: Nina
authors.initials: N
authors.lastname: Gonnella
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA.
authors.forename: Carl A
authors.initials: CA
authors.lastname: Busacca
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT, 06877-0368, USA.
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D002247:Carbon Isotopes / Q000737:chemistry*; D002250:Carbon Radioisotopes / Q000737:chemistry*; D002384:Catalysis; D000069604:Dabigatran / Q000737:chemistry*; D007553:Isotope Labeling; D014316:Tritium / Q000737:chemistry*
chemical_list: D002247:Carbon Isotopes; D002250:Carbon Radioisotopes; D014316:Tritium; D000069604:Dabigatran
keywords: anticoagulant; carbon-13; carbon-14; dabigatran; dabigatran etexilate; pradaxa; tritium