2,6-Difluorobenzoic acid → 2,6-Difluoro-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

HRID 1750600Notes

Reaction equation

HRID 1750600 reaction equation
N1(C2C=CC=CC=2C(N[C@H]2CCC[C@@H]2NC2C=NC(C(F)(F)F)=CN=2)=O)C=CC=N1.Cl.[F:32][C:33]([F:48])([F:47])[C:34]1[N:35]=[CH:36][C:37]([NH:40][C@H:41]2[CH2:45][CH2:44][CH2:43][C@@H:42]2[NH2:46])=[N:38][CH:39]=1.[F:49][C:50]1[CH:58]=[CH:57][CH:56]=[C:55]([F:59])[C:51]=1[C:52](O)=[O:53]>>[F:49][C:50]1[CH:58]=[CH:57][CH:56]=[C:55]([F:59])[C:51]=1[C:52]([NH:46][C@H:42]1[CH2:43][CH2:44][CH2:45][C@@H:41]1[NH:40][C:37]1[CH:36]=[N:35][C:34]([C:33]([F:32])([F:47])[F:48])=[CH:39][N:38]=1)=[O:53]

Participants

4

Reactant 3

HCID 97962,6-Difluorobenzoic acidHCID 118308118(1S,2S)-1-N-[5-(Trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 1183082302-(1H-Pyrazol-1-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Product 1

HCID 1183083232,6-Difluoro-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Procedure

Prepared according to the procedure for 2-(1H-pyrazol-1-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide (Example 31) from (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14, 213 mg, 0.75 mmol) and 2,6-difluorobenzoic acid (CAS number 385-00-2; 131 mg, 0.83 mmol) to afford the title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c58526b4bdda4757b41ebc27ae6199e6
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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