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

HRID 1750645Notes

Reaction equation

HRID 1750645 reaction equation
[CH3:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18][C:19]([C:21]2[C:26]([N:27]3[N:31]=[CH:30][CH:29]=[N:28]3)=[CH:25][CH:24]=[CH:23]N=2)=[O:20])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.Cl.[CH3:33]N(C1C=NC(C(F)(F)F)=CN=1)[C@H]1CCC[C@@H]1N.N1N(C2C=CC=CC=2C(O)=O)N=CC=1>>[CH3:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18][C:19](=[O:20])[C:21]2[CH:33]=[CH:23][CH:24]=[CH:25][C:26]=2[N:27]2[N:28]=[CH:29][CH:30]=[N:31]2)=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[N:7]=1

Participants

4

Reactant 3

HCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acidHCID 118308127(1S,2S)-1-N-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 118308165N-[(1S,2S)-2-{[3-Methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

Product 1

HCID 118308298N-[(1S,2S)-2-{[3-Methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-{[3-methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide (Example 76) from (1S,2S)-1-N-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 23; 60 mg, 0.20 mmol) and 2-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1001401-62-2; 40 mg, 0.21 mmol) except this was purified only by column chromatography (silica, 0 to 100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was purified only by column chromatography (silica, 0 to 100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-101bafba33274dc38194bd38650156cc
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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