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

HRID 1750609Notes

Reaction equation

HRID 1750609 reaction equation
CO[C:3]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:4]=1[C:5]([NH:7][C@H:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[NH:13][C:14]1[CH:19]=[N:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1)=[O:6].Cl.FC(F)(F)C1N=CC(N[C@H]2CCC[C@@H]2N)=NC=1.CC1C=CC([N:57]2[CH:61]=[CH:60][N:59]=[N:58]2)=C(C=1)C(O)=O>>[CH3:28][C:25]1[CH:26]=[CH:27][C:3]([N:57]2[CH:61]=[CH:60][N:59]=[N:58]2)=[C:4]([CH:24]=1)[C:5]([NH:7][C@H:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[NH:13][C:14]1[CH:19]=[N:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=1)=[O:6]

Participants

4

Reactant 3

HCID 583989735-methyl-2-(1H-1,2,3-triazol-1-yl)benzoic acidHCID 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 1183082395-Methyl-2-(1H-1,2,3-triazol-1-yl)-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 5-methyl-2-(1H-1,2,3-triazol-1-yl)benzoic acid (CAS number 1149352-55-5; 65 mg, 0.32 mmol) to afford the title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1b3d8eba16584a66b2b1f40546fbb3c1
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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