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

HRID 1750650Notes

Reaction equation

HRID 1750650 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][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.NC1(C)CCCC1NC(=O)C1C=CC=CC=1N1N=CC=N1.ClC1C=NC(C(F)(F)F)=CN=1>>[CH3:1][C@@:2]1([NH:21][C:22]2[CH:27]=[N:26][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:24][N:23]=2)[CH2:6][CH2:5][CH2:4][C@H: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

Participants

4

Reactant 3

HCID 189876452-Chloro-5-(trifluoromethyl)pyrazineHCID 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 118308220N-[(1R,2R)-2-Methyl-2-{[5-(trifluoromethyl)pyrazin-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; 287 mg, 1.01 mmol) and 2-chloro-5-(trifluoromethyl)pyrazine (CAS number 799557-87-2; 202 mg, 1.11 mmol) except this was then chirally separated using SFC (Waters prep30/MS system using 20% Ethanol, column AY) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was then chirally separated

Sources & evidence

ORD record
ord-1bd69efc85e2456889c14a71cf15dc01
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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