2-(4-Aminophenyl)acetamide → HCID 118037399, compound

HRID 1508834Notes

Reaction equation

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

Participants

Reactant 2

HCID 2380342-(4-Aminophenyl)acetamide

HCID 118036999HCID 118036999, compound

Product 1

HCID 118037399HCID 118037399, compoundYield 18%

Procedure

Following General Procedure A1, 4-chloro-2-(3,5-dichlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine hydrochloride (0.100 g, 0.33 mmol) was reacted with 2-(4-aminophenyl)acetamide (0.060 g, 0.40 mmol), followed by the formation of the hydrochloride salt to afford the title compound (0.024 g, 18%) as a tan solid. MW=448.77. 1H NMR (DMSO-d6, 500 MHz) δ 14.12 (s, 1H), 9.53 (s, 1H), 7.89 (d, J=2.0 Hz, 2H), 7.81 (s, 1H), 7.36 (s, 4H), 7.13 (s, 1H), 3.73 (s, 2H), 3.63 (s, 2H), 3.11 (t, J=7.6 Hz, 2H), 2.91 (t, J=7.6 Hz, 2H), 2.30-2.14 (m, 2H); APCI MS m/z 412 [M+H]+.

Sources & evidence

ORD record: ord-f63c8d2378b2465093db482b59a8d56a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221843B2

Reaction notes

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