Semicarbazide hydrochloride → [(E)-1-[3-(quinolin-6-ylmethyl)imidazo[1,2-a]pyrimidin-6-yl]ethylideneamino]urea

HRID 456120Notes

Reaction equation

HRID 456120 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]3[N:16]4[CH:17]=[C:18]([C:21](=O)[CH3:22])[CH:19]=[N:20][C:15]4=[N:14][CH:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH:25]([C:27]([NH2:29])=[O:28])[NH2:26]>CO>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]3[N:16]4[CH:17]=[C:18](/[C:21](=[N:26]/[NH:25][C:27]([NH2:29])=[O:28])/[CH3:22])[CH:19]=[N:20][C:15]4=[N:14][CH:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11236Semicarbazide hydrochlorideHCID 581904831-(3-(Quinolin-6-ylmethyl)imidazo[1,2-a]pyrimidin-6-yl)ethanone

Product 1

HCID 50916165[(E)-1-[3-(quinolin-6-ylmethyl)imidazo[1,2-a]pyrimidin-6-yl]ethylideneamino]ureaYield 8.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(3-(quinolin-6-ylmethyl)imidazo[1,2-a]pyrimidin-6-yl)ethanone (40 mg, 0.132 mmol) and hydrazinecarboxamide hydrochloride (14.9 mg, 0.198 mmol) in methanol (3 mL) was stirred at 40° C. for 2 h. The solvent was removed in vacuo and the residue was purified by HPLC to afford 4.2 mg (8.8%) of the title compound as white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.45 (s, 1H), 9.24 (d, 1H), 8.91 (d, 1H), 8.86 (dd, 1H), 8.30 (d, 1H), 7.98 (d, 1H), 7.89 (s, 1H), 7.72 (dd, 1H), 7.52-7.49 (m, 2H), 6.65 (s, 2H), 4.59 (s, 2H), 2.18 (s, 3H). LCMS (method A): [MH]+=360, tR=2.95 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-e21e2fb187a745d1b425b3ef9d19e2e7
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

Loading…