4-Aminophenethyl alcohol → 2-(4-((2-(3-Chloro-5-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)ethanol hydrochloride

HRID 1508827Notes

Reaction equation

HRID 1508827 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]=[C:6]([F:8])[CH:7]=1.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:24]=[CH:23][C:22]([CH2:25][CH2:26][OH:27])=[CH:21][CH:20]=3)[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 2

HCID 669044-Aminophenethyl alcoholHCID 118037106ethyl 2-(4-((2-(3-chloro-5-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)acetate

Product 1

HCID 901105162-(4-((2-(3-Chloro-5-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)ethanol hydrochlorideYield 30%

Procedure

Following General Procedure B2, ethyl 2-(4-((2-(3-chloro-5-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-4-yl)amino)phenyl)acetate (0.075 g, 0.27 mmol) was reacted with 4-aminophenethyl alcohol (0.055 g, 0.40 mmol), followed by the formation of the hydrochloride salt to afford the title compound (0.017 g, 23%) as a yellow solid. MW=419.32. 1H NMR (DMSO-d6, 300 MHz) δ 14.06 (s, 1H), 9.77 (s, 1H), 7.79-7.76 (m, 1H), 7.75-7.72 (m, 1H), 7.71-7.68 (m, 1H), 7.33 (s, 4H), 7.05 (s, 1H), 3.64 (t, J=6.9 Hz, 3H), 3.15 (t, J=7.6 Hz, 2H), 2.92 (t, J=7.6 Hz, 2H), 2.76 (t, J=6.9 Hz, 2H), 2.30-2.17 (m, 2H); APCI MS m/z 383 [M+H]+.

Sources & evidence

ORD record
ord-dcddf59201b74969a12b0f168c8f3e8b
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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