Ammonium Hydroxide → 2-(6-Bromo-7-(4-(2-oxo-2-(thiazol-2-ylamino)ethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)cyclopropanecarboxamide

HRID 416765Notes

Reaction equation

[Br:1][C:2]1[C:3]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][C:26](=[O:33])[NH:27][C:28]3[S:29][CH:30]=[CH:31][N:32]=3)[CH2:21][CH2:20]2)=[C:4]2[N:10]=[C:9]([CH:11]3[CH2:13][CH:12]3[C:14]([O:16]CC)=O)[NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[NH4+:35]>>[Br:1][C:2]1[C:3]([N:19]2[CH2:20][CH2:21][N:22]([CH2:25][C:26](=[O:33])[NH:27][C:28]3[S:29][CH:30]=[CH:31][N:32]=3)[CH2:23][CH2:24]2)=[C:4]2[N:10]=[C:9]([CH:11]3[CH2:13][CH:12]3[C:14]([NH2:35])=[O:16])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 178468466HCID 178468466, compound

Product 1

HCID 1785134802-(6-Bromo-7-(4-(2-oxo-2-(thiazol-2-ylamino)ethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)cyclopropanecarboxamide

Procedure

A solution of ethyl 2-(6-bromo-7-(4-(2-oxo-2-(thiazol-2-ylamino)ethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)cyclopropanecarboxylate (15 mg, 0.028 mmol) in ammonium hydroxide (2.5 mL) was heated in a sealed tube at 100° C. for 16 h. After this time, LC-MS analysis showed that only the desired product was present. Evaporation of the solvents in vacuo provided the product (9 mg, 64%) as a colourless solid; 1H-NMR (500 MHz, DMSO-d6) 1.40 (app. quintet, J=4.4 Hz, 1H, cyclopropane CHAHB), 1.46-1.51 (m, 1H, cyclopropane CHAHB), 2.20-2.24 (m, 1H, cyclopropane CH), 2.40 (br s, 1H, cyclopropane CH), 2.74 (t, J=4.9 Hz, 4H, piperazine N(CH2)2), 3.38 (s, 2H, NCH2CO), 3.54 (br s, 4H, piperazine N(CH2)2), 6.53 (d, J=3.7 Hz, 1H, thiazole H-4 or H-5), 6.83 (br s, 2H, NH2), 6.92 (d, J=3.7 Hz, 1H, thiazole H-4 or H-5), 7.02 (br s, 1H, CONH), 7.74 (br s, 1H, imidazo[4,5-b]pyridine H-5);

Sources & evidence

ORD record: ord-6d0b7e716e0c4cccbcf6065411ed6eca
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088761B2

Reaction notes

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