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

HRID 1750642Notes

Reaction equation

HRID 1750642 reaction equation
[CH3:1][N:2]([C:22]1[CH:27]=[N:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=1)[C@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[N:20]=[CH:19][CH:18]=[N:17]1.CN(C1C=NC(C(F)(F)[F:47])=CN=1)[C@H]1CCC[C@@H]1N.FC1C=CC=C(N2N=CC=N2)C=1C(O)=O>>[F:47][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([N:16]2[N:20]=[CH:19][CH:18]=[N:17]2)[C:10]=1[C:9]([NH:8][C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:3]1[N:2]([CH3:1])[C:22]1[CH:27]=[N:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][N:23]=1)=[O:21]

Participants

4

Reactant 3

HCID 670866272-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acidHCID 118308113(1S,2S)-1-N-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine2×HCID 118308125N-[(1S,2S)-2-{Methyl[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

Product 1

HCID 1183082152-Fluoro-N-[(1S,2S)-2-{methyl[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[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Example 73) from (1S,2S)-1-N-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 22; 59 mg, 0.23 mmol) and 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1186050-58-7; 56 mg, 0.27 mmol) to afford the title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-60883352e2ae4835b15d163c354d6288
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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