Methyl 2-(4-aminophenoxy)propanoate → HCID 90338570, compound

HRID 1508762Notes

Reaction equation

HRID 1508762 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[N:5]=[C:4]2[CH2:15][CH2:16][CH2:17][C:3]=12.[NH2:18][C:19]1[CH:31]=[CH:30][C:22]([O:23][CH:24]([CH3:29])[C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=1>>[Cl:14][C:10]1[CH:9]=[C:8]([C:6]2[N:5]=[C:4]3[CH2:15][CH2:16][CH2:17][C:3]3=[C:2]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([O:23][CH:24]([CH3:29])[C:25]([O:27][CH3:28])=[O:26])=[CH:30][CH:31]=3)[CH:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 22060471Methyl 2-(4-aminophenoxy)propanoateHCID 901106754-chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 90338570HCID 90338570, compoundYield 97%

Procedure

Following General Procedure B2, 4-chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine (0.150 g, 0.57 mmol) was reacted with methyl 2-(4-aminophenoxy)propanoate (0.133 g, 0.68 mmol) to afford the title compound (0.146 g, 97%) as an off-white solid. MW=422.90. 1H NMR (DMSO-d6, 500 MHz) δ 7.98 (s, 1H), 7.88-7.86 (m, 1H), 7.74-7.69 (m, 1H), 7.46-7.38 (m, 2H), 7.22-7.17 (m, 2H), 7.02 (s, 1H), 6.96-6.89 (m, 2H), 4.96 (q, J=6.8 Hz, 1H), 3.69 (s, 3H), 2.89 (t, J=7.6 Hz, 2H), 2.80 (t, J=7.6 Hz, 2H), 2.13-2.03 (m, 2H), 1.51 (d, J=6.7 Hz, 3H); APCI MS m/z 423 [M+H]+.

Sources & evidence

ORD record
ord-22dbeb929b314a5b9f99e27c45c6839d
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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