(R)-4,4-Difluoropyrrolidine-2-carboxamide hydrochloride → (R)-1-[5-Cyclopropyl-6-(2,2,3,3,3-pentafluoro-propoxy)-pyridine-2-carbonyl]-4,4-difluoro-pyrrolidine-2-carboxylic acid amide

HRID 624952Notes

Reaction equation

HRID 624952 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:19]([OH:21])=O)=[N:8][C:9]=2[O:10][CH2:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[CH2:3][CH2:2]1.Cl.[F:23][C:24]1([F:32])[CH2:28][NH:27][C@@H:26]([C:29]([NH2:31])=[O:30])[CH2:25]1>>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:19]([N:27]3[CH2:28][C:24]([F:32])([F:23])[CH2:25][C@@H:26]3[C:29]([NH2:31])=[O:30])=[O:21])=[N:8][C:9]=2[O:10][CH2:11][C:12]([F:17])([F:18])[C:13]([F:14])([F:16])[F:15])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 45158907(R)-4,4-Difluoropyrrolidine-2-carboxamide hydrochlorideHCID 866747875-Cyclopropyl-6-(2,2,3,3,3-pentafluoro-propoxy)-pyridine-2-carboxylic acid

Product 1

HCID 76280801(R)-1-[5-Cyclopropyl-6-(2,2,3,3,3-pentafluoro-propoxy)-pyridine-2-carbonyl]-4,4-difluoro-pyrrolidine-2-carboxylic acid amide

Procedure

The title compound was synthesized in analogy to Example 47 b, using 5-cyclopropyl-6-(2,2,3,3,3-pentafluoro-propoxy)-pyridine-2-carboxylic acid (30 mg, 96 μmol) and (2R)-4,4-difluoropyrrolidine-2-carboxamide hydrochloride (CAN 1315053-41-8; 19.8 mg, 106 μmol) as starting materials and isolated (38 mg, 89%) as white solid; LC-MS (UV peak area, ESI) 97%, 444.1155 [MH+].

Workup

  1. customisolated (38 mg, 89%) as white solid

Sources & evidence

ORD record
ord-571be7060ceb4d15b1745ad91db30453
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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