2-(4-Aminophenyl)acetamide → Benzeneacetamide, 4-((2-(3-chlorophenyl)-6-(trifluoromethyl)-4-pyrimidinyl)amino)-

HRID 1508926Notes

Reaction equation

HRID 1508926 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([NH2:29])=[O:28])=[CH:22][CH:21]=1>>[Cl:18][C:14]1[CH:13]=[C:12]([C:4]2[N:3]=[C:2]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C:27]([NH2:29])=[O:28])=[CH:24][CH:25]=3)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=2)[CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 2380342-(4-Aminophenyl)acetamideHCID 755282424-Chloro-2-(3-chlorophenyl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 77461017Benzeneacetamide, 4-((2-(3-chlorophenyl)-6-(trifluoromethyl)-4-pyrimidinyl)amino)-Yield 56%

Procedure

Following General Procedure A2, 4-chloro-2-(3-chlorophenyl)-6-(trifluoromethyl)pyrimidine (0.100 g, 0.34 mmol) was reacted with 2-(4-aminophenyl)acetamide (0.103 g, 0.68 mmol) to afford the title compound (0.042 g, 56%) as an off-white solid. MW=406.79. 1H NMR (DMSO-d6, 500 MHz) δ 10.24 (s, 1H), 8.33-8.25 (m, 2H), 7.74-7.58 (m, 4H), 7.33 (d, J=8.5 Hz, 2H), 7.09 (s, 1H), 6.88 (s, 1H), 3.39 (s, 2H), 2.70 (s, 1H); APCI MS m/z 407 [M+H]+.

Sources & evidence

ORD record
ord-0b6677c655984ef58c387df522e02ff0
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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