Ammonia → HCID 118037247, compound

HRID 1508820Notes

Reaction equation

HRID 1508820 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[CH2:14][CH2:15][CH2:16][C:11]3=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27]CC)=O)=[CH:20][CH:19]=3)[CH:9]=2)=[CH:4][CH:3]=1.[NH3:30]>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]3[CH2:14][CH2:15][CH2:16][C:11]3=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH2:30])=[O:27])=[CH:20][CH:19]=3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 90338543HCID 90338543, compound

Product 1

HCID 118037247HCID 118037247, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following General Procedure C, ethyl 2-(4-((2-(4-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-4-yl)amino)phenyl)acetate (0.075 g, 0.18 mmol) was reacted with ammonia in methanol (7 M, 4 mL), followed by the formation of the hydrochloride salt to form the title compound (0.017 g, 22%) as an off-white solid. MW=414.33. 1H NMR (DMSO-d6, 300 MHz) δ 14.03 (s, 1H), 9.80 (s, 1H), 7.83-7.75 (m, 2H), 7.70-7.63 (m, 2H), 7.54 (s, 1H), 7.42-7.30 (m, 4H), 6.98 (s, 1H), 6.94 (s, 1H), 3.42 (s, 2H), 3.16 (t, J=7.6 Hz, 2H), 2.92 (t, J=7.6 Hz, 2H), 2.31-2.18 (m, 2H); APCI MS m/z 378 [M+H]+.

Sources & evidence

ORD record
ord-2f1005c275d94e8baf7a67d934b1712b
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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