1-Methylpyrrolidine → HCID 178482686, compound

HRID 416761Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:12])OC(C)=C.[Br:13][C:14]1[C:15]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[C:16]2[N:22]=[C:21]([C:23]3[CH:31]=[CH:30][C:26]([N:27]([CH3:29])[CH3:28])=[CH:25][CH:24]=3)[NH:20][C:17]2=[N:18][CH:19]=1.CN1CCCC1>C1COCC1>[Br:13][C:14]1[C:15]([N:32]2[CH2:33][CH2:34][N:35]([C:7]([NH:6][C:2]3[S:1][CH:5]=[CH:4][N:3]=3)=[O:12])[CH2:36][CH2:37]2)=[C:16]2[N:22]=[C:21]([C:23]3[CH:31]=[CH:30][C:26]([N:27]([CH3:29])[CH3:28])=[CH:25][CH:24]=3)[NH:20][C:17]2=[N:18][CH:19]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of prop-1-en-2-yl thiazol-2-ylcarbamate (prepared according to the procedure described in J. Org. Chem. 2005, 70, 6960-6963) (40 mg, 0.054 mmol) and 4-(6-bromo-7-(piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline (1.0 eq, 0.054 mmol, 22 mg) in THF (0.5 mL) was heated to 55° C. Then N-methylpyrrolidine (0.1 eq, 0.005 mmol, 5 μL) was added and the mixture stirred at 55° C. for 2 h. Concentration in vacuo gave crude material as a solid. A small sample was purified by semi-preparative hplc to give the pure product as a colourless solid; 1H-NMR (500 MHz, DMSO-d6) 2.99 (s, 6H, N(CH3)2), 3.58-3.62 (m, 4H, piperazine N(CH2)2), 3.74-3.78 (m, 4H, piperazine N(CH2)2), 6.81 (d, J=8.9 Hz, 2H, N,N-dimethylaminophenyl), 7.22 (d, J=3.6 Hz, 1H, thiazole H-4 or H-5), 7.35 (br s, 1H, NH), 7.48 (d, J=3.6 Hz, 1H, thiazole H-4 or H-5), 8.02 (d, J=8.9 Hz, 2H, N,N-dimethylaminophenyl), 8.19 (s, 1H, imidazo[4,5-b]pyridine H-5).

Workup

concentrationConcentration in vacuo
customgave crude material as a solid
customA small sample was purified by semi-preparative hplc

Sources & evidence

ORD record: ord-cd985a8885a142218062189e18dec11b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088761B2

Reaction notes

Loading…