3,3-Difluoropyrrolidine hydrochloride → 5-(3,3-Difluoro-pyrrolidin-1-yl)-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [1-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

HRID 1480143Notes

Reaction equation

HRID 1480143 reaction equation
[CH:1]1([C:4]([NH:12][C:13]([C:15]2[CH:20]=[C:19]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[C:18](Br)=[CH:17][N:16]=2)=[O:14])([C:6]2[N:10]=[C:9]([CH3:11])[O:8][N:7]=2)[CH3:5])[CH2:3][CH2:2]1.Cl.[F:29][C:30]1([F:35])[CH2:34][CH2:33][NH:32][CH2:31]1>>[CH:1]1([C:4]([NH:12][C:13]([C:15]2[CH:20]=[C:19]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[C:18]([N:32]3[CH2:33][CH2:34][C:30]([F:35])([F:29])[CH2:31]3)=[CH:17][N:16]=2)=[O:14])([C:6]2[N:10]=[C:9]([CH3:11])[O:8][N:7]=2)[CH3:5])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 249034823,3-Difluoropyrrolidine hydrochlorideHCID 902039835-Bromo-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [1-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

Product 1

HCID 762837005-(3,3-Difluoro-pyrrolidin-1-yl)-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [1-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

Procedure

The title compound was synthesized in analogy to Example 78h, using 5-Bromo-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [1-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide (Example 78g) and 3,3-difluoropyrrolidine hydrochloride (CAN 163457-23-6) as starting materials and isolated (17 mg, 32%) as a white solid; MS (ESI, m/z): 476.4 (M+H+).

Workup

  1. customisolated (17 mg, 32%) as a white solid

Sources & evidence

ORD record
ord-0defbffae8344d76bd2d4e09e252e841
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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