Ammonia → HCID 90338622, compound

HRID 1508968Notes

Reaction equation

HRID 1508968 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]=[C:10]3[CH2:12][CH2:13][CH2:14][C:9]3=[C:8]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25]CC)=O)=[CH:18][CH:17]=3)[CH:7]=2)=[CH:2]1.[NH3:28]>CO>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]=[C:10]3[CH2:12][CH2:13][CH2:14][C:9]3=[C:8]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH2:22][C:23]([NH2:28])=[O:25])=[CH:20][CH:21]=3)[CH:7]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 90113139HCID 90113139, compound

Product 1

HCID 90338622HCID 90338622, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following general procedure C, ethyl 2-(4-((2-(thiophen-3-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)acetate (0.065 g, 0.17 mmol) was reacted with ammonia in methanol (7.0 M, 5 mL), followed by formation of the hydrochloride salt to afford the title compound (0.033 g, 50%) as a light yellow solid. MW=385.91. 1H NMR (DMSO-d6, 500 MHz) δ 13.84 (s, 1H), 9.69 (s, 1H), 8.35-8.31 (m, 1H), 7.81-7.76 (m, 1H), 7.59-7.56 (m, 1H), 7.51 (s, 1H), 7.38 (d, J=8.5 Hz, 2H), 7.33 (d, J=8.5 Hz, 2H), 7.05 (s, 1H), 6.92 (s, 1H), 3.43 (s, 2H), 3.15 (t, J=7.5 Hz, 2H), 2.89 (t, J=7.5 Hz, 2H), 2.23 (quin, J=7.5 Hz, 2H); APCI MS m/z 350 [M+H]+.

Sources & evidence

ORD record
ord-012e06f19d5d42e3ae352f29a2958317
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

Loading…