Ethyl isocyanate → HCID 178465278, compound

HRID 416762Notes

Reaction equation

HRID 416762 reaction equation
[Br:1][C:2]1[C:3]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[CH2:26]([N:28]=[C:29]=[O:30])[CH3:27]>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([N:20]2[CH2:21][CH2:22][N:23]([C:29]([NH:28][CH2:26][CH3:27])=[O:30])[CH2:24][CH2:25]2)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 178482665HCID 178482665, compound

Product 1

HCID 178465278HCID 178465278, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

This was prepared from [4-(6-bromo-7-piperazin-1-yl-3H-imidazo[4,5-b]pyridin-2-yl)-phenyl]-dimethyl-amine (20 mg, 0.050 mmol), using CHCl3 (1.5 mL) and ethyl isocyanate (1.1 eq, 0.055 mmol, 43 μL). Filtration of the precipitate after 16 h gave the product (13 mg, 56%) as a pale yellow solid; 1H-NMR (500 MHz, DMSO-d6) 1.05 (t, J=7.1 Hz, 3H, CH2CH3), 3.00 (s, 6H, N(CH3)2), 3.09 (qd, J=7.1, 5.4 Hz, 2H, NHCH2), 3.50-3.52 (m, 4H, piperazine N(CH2)2), 3.55-3.57 (4H, m, piperazine N(CH2)2), 6.55 (t, J=5.4 Hz, 1H, NHCH2), 6.82 (d, J=9.0 Hz, 2H, N,N-dimethylaminophenyl), 8.01 (d, J=9.0 Hz, 2H, N,N-dimethylaminophenyl), 8.17 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.18 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. filtrationFiltration of the precipitate after 16 h

Sources & evidence

ORD record
ord-49e57b9413c94a389aaee2ca920a30ab
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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