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

HRID 1508997Notes

Reaction equation

HRID 1508997 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[N:5]=[C:4]2[CH2:12][CH2:13][CH2:14][C:3]=12.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][CH:17]=1>>[CH:9]([O:8][C:6]1[N:5]=[C:4]2[CH2:12][CH2:13][CH2:14][C:3]2=[C:2]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:21]=2)[CH:7]=1)([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 901123734-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 90338576ethyl 2-(4-((2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)acetateYield 86%

Procedure

Following general procedure B1, 4-chloro-2-isopropoxy-6,7-dihydro-5H-cyclopenta[b]pyridine (0.090 g, 0.43 mmol) was reacted with ethyl 2-(4-aminophenyl)acetate (0.114 g, 0.64 mmol) to afford the title compound (0.130 g, 86%) as a yellow gel. MW=354.44. APCI MS m/z 355 [M+H]+.

Sources & evidence

ORD record
ord-4a4690546dfc4d85be46e4814fead9eb
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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