2-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)benzoic acid → 2-(2H-1,2,3-Triazol-2-yl)-5-(trifluoromethyl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

HRID 1750612Notes

Reaction equation

HRID 1750612 reaction equation
COC1C=CC(C)=CC=1C(N[C@H]1CCC[C@@H]1NC1C=NC(C(F)(F)F)=CN=1)=O.Cl.[F:30][C:31]([F:46])([F:45])[C:32]1[N:33]=[CH:34][C:35]([NH:38][C@H:39]2[CH2:43][CH2:42][CH2:41][C@@H:40]2[NH2:44])=[N:36][CH:37]=1.[N:47]1[N:48]([C:52]2[CH:60]=[CH:59][C:58]([C:61]([F:64])([F:63])[F:62])=[CH:57][C:53]=2[C:54](O)=[O:55])[N:49]=[CH:50][CH:51]=1>>[N:47]1[N:48]([C:52]2[CH:60]=[CH:59][C:58]([C:61]([F:62])([F:63])[F:64])=[CH:57][C:53]=2[C:54]([NH:44][C@H:40]2[CH2:41][CH2:42][CH2:43][C@@H:39]2[NH:38][C:35]2[CH:34]=[N:33][C:32]([C:31]([F:30])([F:45])[F:46])=[CH:37][N:36]=2)=[O:55])[N:49]=[CH:50][CH:51]=1

Participants

4

Reactant 3

HCID 679821772-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)benzoic acid2×HCID 118308118(1S,2S)-1-N-[5-(Trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 1183082742-Methoxy-5-methyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Product 1

HCID 1183083462-(2H-1,2,3-Triazol-2-yl)-5-(trifluoromethyl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Procedure

Prepared according to the procedure for 2-methoxy-5-methyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide (Example 37) from (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14; 75 mg, 0.27 mmol) and 2-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)benzoic acid (Intermediate 37a; CAS number 1384066-81-2; 94 mg, 0.37 mmol) except this was purified by column chromatography (silica, 40-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was purified by column chromatography (silica, 40-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-55c0075af1e648ac8ae4058ea6f6f34a
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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