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

HRID 1750661Notes

Reaction equation

HRID 1750661 reaction equation
[CH3:1][C:2]1([NH:21][C:22]2[CH:27]=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.N[C:34]1(C)CCCC1NC(=O)C1C=CC=CC=1N1N=CC=N1.ClC1C=CC(C(F)(F)F)=CN=1>>[CH3:1][C:2]1([NH:21][C:22]2[CH:27]=[CH:34][C:25]([C:28]([F:29])([F:30])[F:31])=[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:16]=[CH:17][CH:18]=[N:19]1

Participants

4

Reactant 3

HCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 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 118308287N-(2-Methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide

Conditions

Temperature
140 °C

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; 95 mg, 0.30 mmol) and 2-chloro-5-(trifluoromethyl)pyridine (CAS number 52334-81-3; 100 mg, 0.55 mmol) except this was heated at 140° C. for 17 hours and then purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customPrepared
  2. custompurified by column chromatography (basic silica, 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-40a6d0b473d1462ca07fadb6d1e694f3
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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