4-Aminophenethyl alcohol → HCID 118037343, compound

HRID 1508824Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]3[CH2:15][CH2:16][CH2:17][C:12]3=[C:11]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26](OCC)=[O:27])=[CH:21][CH:20]=3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].NC1C=CC(CCO)=CC=1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]3[CH2:15][CH2:16][CH2:17][C:12]3=[C:11]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][OH:27])=[CH:23][CH:24]=3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Reactant 2

HCID 669044-Aminophenethyl alcohol

HCID 90112554HCID 90112554, compound

Product 1

HCID 118037343HCID 118037343, compoundYield 15%

Procedure

Following General Procedure B2, ethyl 2-(4-((2-(3-chloro-4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-4-yl)amino)phenyl)acetate (0.110 g, 0.39 mmol) was reacted with 4-aminophenethyl alcohol (0.080 g, 0.58 mmol), followed by the formation of the hydrochloride salt to afford the title compound (0.011 g, 15%) as an off-white solid. MW=405.29. 1H NMR (DMSO-d6, 300 MHz) δ 14.04 (s, 1H), 9.74 (s, 1H), 8.18-8.01 (m, 1H), 7.81-7.72 (m, 1H), 7.64 (t, J=8.9 Hz, 1H), 7.38-7.27 (m, 4H), 6.99 (s, 1H), 3.64 (t, J=6.8 Hz, 2H), 3.14 (t, J=7.6 Hz, 2H), 2.92 (t, J=7.6 Hz, 2H), 2.76 (t, J=6.8 Hz, 2H) 2.31-2.16 (m, 2H), 1.24 (s, 1H); APCI MS m/z 383 [M+H]+.

Sources & evidence

ORD record: ord-e91d06a46e7b47efae95852948c4c709
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221843B2

Reaction notes

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