Ammonia → HCID 90338553, compound

HRID 1508964Notes

Reaction equation

HRID 1508964 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:11]=[C:10]2[CH2:12][CH2:13][CH2:14][C:9]2=[C:8]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25]CC)=O)=[CH:18][CH:17]=2)[CH:7]=1.[NH3:28]>CO>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[N:11]=[C:10]2[CH2:12][CH2:13][CH2:14][C:9]2=[C:8]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([NH2:28])=[O:25])=[CH:18][CH:17]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 90338679HCID 90338679, compound

Product 1

HCID 90338553HCID 90338553, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following general procedure C, ethyl 2-(4-((2-(oxazol-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)acetate (0.047 g, 0.13 mmol) was reacted with ammonia in methanol (7.0 M, 5 mL) to afford the title compound (0.027 g, 63%) as a white solid. MW=334.37. 1H NMR (DMSO-d6, 500 MHz) δ 8.24 (s, 1H), 8.16 (s, 1H), 7.49-7.43 (m, 2H), 7.32-7.25 (m, 3H), 7.17 (d, J=8.5 Hz, 2H), 6.87 (s, 1H), 3.37 (s, 2H), 2.90 (t, J=7.5 Hz, 2H), 2.85 (t, J=7.5 Hz, 2H), 2.09 (quin, J=7.5 Hz, 2H); APCI MS m/z 335 [M+H]+.

Sources & evidence

ORD record
ord-677cf79f83a2489e879e6ce18c174228
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

Loading…