2-Chloro-5-(trifluoromethyl)pyrimidine → N-(2-Methyl-2-{[5-(trifluoromethyl)pyrimidin-2-yl]amino}cyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide

HRID 1750660Notes

Reaction equation

HRID 1750660 reaction equation
[CH3:1][C:2]1([NH:21][C:22]2C=N[C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][C:8](=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[N:19]=[CH:18][CH:17]=[N:16]1.Cl.[NH2:33][C:34]1(C)CCCC1NC(=O)C1C=CC=CC=1N1N=CC=N1.ClC1N=CC(C(F)(F)F)=CN=1>>[CH3:1][C:2]1([NH:21][C:22]2[N:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:34][N:33]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][C:8](=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[N:16]=[CH:17][CH:18]=[N:19]1

Participants

4

Reactant 3

HCID 133170192-Chloro-5-(trifluoromethyl)pyrimidineHCID 118025536N-(2-Amino-2-methylcyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride2×HCID 118308141N-(2-Methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide

Product 1

HCID 118308234N-(2-Methyl-2-{[5-(trifluoromethyl)pyrimidin-2-yl]amino}cyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide

Procedure

Prepared according to the procedure for N-(2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide (Example 82) from N-(2-amino-2-methylcyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 26; 200 mg, 0.70 mmol) and 2-chloro-5-(trifluoromethyl)pyrimidine (CAS number 69034-12-4; 141 mg, 0.77 mmol) except this was purified by column chromatography (silica, 0-100% ethyl acetate/petrol) followed by reverse phase chromatography (C18 silica, 0-100% water (with 0.05% ammonia)/acetonitrile) to afford the title compound.

Workup

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

Sources & evidence

ORD record
ord-9357da93581c4f0b8c91014021694910
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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