2-Chloro-6-(2H-1,2,3-triazol-2-yl)benzoic acid → 2-Chloro-N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-6-(2H-1,2,3-triazol-2-yl)benzamide

HRID 1750654Notes

Reaction equation

HRID 1750654 reaction equation
[CH3:1][C@:2]1([NH:21][C:22]2[CH:27]=[N:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=2)[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8]([C:10]1[C:15]([N:16]2[N:20]=[CH:19][CH:18]=[N:17]2)=[CH:14][CH:13]=[CH:12]N=1)=[O:9].C[C@]1(NC2C=NC(C(F)(F)F)=CN=2)CCC[C@@H]1N.[Cl:50][C:51]1C=CC=C(N2N=CC=N2)C=1C(O)=O>>[Cl:50][C:51]1[CH:12]=[CH:13][CH:14]=[C:15]([N:16]2[N:20]=[CH:19][CH:18]=[N:17]2)[C:10]=1[C:8]([NH:7][C@H:3]1[CH2:4][CH2:5][CH2:6][C@:2]1([CH3:1])[NH:21][C:22]1[CH:27]=[N:26][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:24][N:23]=1)=[O:9]

Participants

4

Reactant 3

HCID 846887842-Chloro-6-(2H-1,2,3-triazol-2-yl)benzoic acid2×HCID 118308048(1S,2S)-1-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine2×HCID 118308152N-[(1S,2S)-2-Methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

Product 1

HCID 1183080452-Chloro-N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-6-(2H-1,2,3-triazol-2-yl)benzamide

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide (Example 77) from (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 63 mg, 0.24 mmol) and 2-chloro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 15; 65 mg, 0.29 mmol) except this was purified by column chromatography (silica, 0-30% ethyl acetate/petrol) followed by trituration with diethyl ether/pentane to afford the title compound.

Workup

  1. customPrepared
  2. customthis was purified by column chromatography (silica, 0-30% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-4ecfd0e727ef4a8d9b2e597dbfd1ecbe
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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