p-Aminophenylacetic acid ethyl ester → ethyl 2-(4-((2-(3-chloro-5-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)acetate

HRID 1508826Notes

Reaction equation

HRID 1508826 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([Cl:15])[CH:9]=2)[N:5]=[C:4]2[CH2:16][CH2:17][CH2:18][C:3]=12.[CH2:19]([O:21][C:22](=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)[CH3:20]>>[Cl:15][C:10]1[CH:9]=[C:8]([C:6]2[N:5]=[C:4]3[CH2:16][CH2:17][CH2:18][C:3]3=[C:2]([NH:30][C:27]3[CH:26]=[CH:25][C:24]([CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:31])=[CH:29][CH:28]=3)[CH:7]=2)[CH:13]=[C:12]([F:14])[CH:11]=1

Participants

3

Reactant 2

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 901122754-chloro-2-(3-chloro-5-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 118037106ethyl 2-(4-((2-(3-chloro-5-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)acetateYield 87%

Procedure

Following General Procedure B2, 4-chloro-2-(3-chloro-5-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine (0.100 g, 0.36 mmol) was reacted with 4-aminophenylacetic acid ethyl ester (0.096 g, 0.53 mmol) to afford the title compound (0.086 g, 87%) as a yellow oil. MW=424.90. 1H NMR (CD3OD, 300 MHz) δ 7.54 (s, 1H), 7.43-7.34 (m, 1H), 7.31 (s, 1H), 7.28 (s, 1H), 7.25-7.13 (m, 3H), 7.10-7.06 (m, 1H), 5.48 (s, 1H), 4.21-4.07 (m, 2H), 3.69 (s, 2H), 2.98 (t, J=7.6 Hz, 2H), 2.86 (t, J=7.6 Hz, 2H), 2.17 (quin, J=7.6, 2H), 1.37-1.17 (m, 3H); APCI MS m/z 425 [M+H]+.

Sources & evidence

ORD record
ord-95f4fbd7283f4b73b202e8fdf4ae7933
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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