Diisopropylcarbodiimide → HCID 178481207, compound

HRID 1410255Notes

Reaction equation

HRID 1410255 reaction equation
[Cl:1][C:2]1[C:9]([N:10]=[C:11]=S)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:13])[CH:3]=1.[NH2:14][C:15]1[C:16]([NH:39][CH3:40])=[CH:17][C:18]([O:34][CH2:35][CH:36]([F:38])[F:37])=[C:19]([CH:33]=1)[C:20]([NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29]([F:32])([F:31])[F:30])[CH2:25][CH2:24]1)=[O:21].CC(C)N=C=NC(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([F:13])[C:5]([C:6]#[N:7])=[CH:8][C:9]=1[NH:10][C:11]1[N:39]([CH3:40])[C:16]2[CH:17]=[C:18]([O:34][CH2:35][CH:36]([F:37])[F:38])[C:19]([C:20]([NH:22][C@H:23]3[CH2:28][CH2:27][C@H:26]([C:29]([F:32])([F:31])[F:30])[CH2:25][CH2:24]3)=[O:21])=[CH:33][C:15]=2[N:14]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 866463424-Chloro-2-fluoro-5-isothiocyanatobenzonitrileHCID 178482270HCID 178482270, compound

Product 1

HCID 178481207HCID 178481207, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sub-title compound was prepared in accordance with the procedure in Example 72, step (a) using 4-chloro-2-fluoro-5-isothiocyanatobenzonitrile (270 mg; 1.27 mmol), 5-amino-2-(2,2-difluoroethoxy)-4-(methylamino)-N-((trans)-4-(trifluoromethyl)cyclohexyl)benzamide [502 mg; 1.27 mmol, prepared from 4-trans-trifluoromethyl-cyclohexylamine and 2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzoic acid in analogy to Example 66, step (f+g)], DIC (160 mg; 1.27 mmol) and DMF (10 mL). Yield: 210 mg (29%).

Sources & evidence

ORD record
ord-7074b6eae0714e2fa8f61a952f497b7e
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

Loading…