2-(4-Aminophenyl)acetamide → 2-(4-((2-Cyclopentyl-6-ethylpyrimidin-4-yl)amino)phenyl)acetamide

HRID 1508930Notes

Reaction equation

HRID 1508930 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([NH2:25])=[O:24])=[CH:18][CH:17]=1>>[CH:10]1([C:4]2[N:3]=[C:2]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH2:22][C:23]([NH2:25])=[O:24])=[CH:20][CH:21]=3)[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 2380342-(4-Aminophenyl)acetamideHCID 609214014-Chloro-2-cyclopentyl-6-ethylpyrimidine

Product 1

HCID 901120042-(4-((2-Cyclopentyl-6-ethylpyrimidin-4-yl)amino)phenyl)acetamideYield 97%

Procedure

Following General Procedure A2, 4-chloro-2-cyclopentyl-6-ethylpyrimidine (0.100 g, 0.47 mmol) was reacted with 2-(4-aminophenyl)acetamide (0.086 g, 0.57 mmol) to afford the title compound (0.097 g, 97%) as a tan solid. MW=324.42. 1H NMR (DMSO-d6, 500 MHz) δ 14.18 (s, 1H), 11.23 (s, 1H), 7.64 (s, 1H), 7.49 (s, 1H), 7.36-7.25 (m, 2H), 6.88 (s, 1H), 6.76 (s, 1H), 3.37 (d, J=7.5 Hz, 3H), 2.82-2.66 (m, 2H), 2.13-1.98 (m, 2H), 1.94-1.73 (m, 4H), 1.72-1.59 (m, 2H), 1.25 (s, 3H); APCI MS m/z 325 [M+H]+.

Sources & evidence

ORD record
ord-38bf182c3f6247a781433c117c5b789f
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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