N-((3R)-1-tert-Butylcarbonylmethyl-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4-benzodiazepin-3-yl)-N'-(3-dimethylaminophenyl)urea → N-((3R)-1-tert-Butylcarbonylmethyl-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4-benzodiazepin-3-yl)-N'-(3-dimethylaminophenyl)urea hydrochloride

HRID 2340

Reaction equation

[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:11][C@@H:10]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N:35]([CH3:37])[CH3:36])[CH:30]=2)=[O:27])[C:9]1=[O:38])=[O:6])([CH3:4])([CH3:3])[CH3:2].C(O)C.[ClH:42]>C(O)C>[ClH:42].[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:11][C@@H:10]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N:35]([CH3:37])[CH3:36])[CH:30]=2)=[O:27])[C:9]1=[O:38])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

N-((3R)-1-tert-Butylcarbonylmethyl-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4-benzodiazepin-3-yl)-N'-(3-dimethylaminophenyl)urea (70 g, 136.6 mmol) was taken up in ethanol (1 l) and 2.26M HCl ethanol (63.5 ml, 143.4 mmol) was added dropwise. The mixture was warmed up to 50° C. to afford a clear solution, which was seeded, cooled to 0° C. and stirred at the same temperature overnight. The resultant precipitate was collected by flirtation to provide the title compound as a white crystalline (62.4 g, 82%): top. 181°-184° C.

Workup

customto afford a clear solution, which
temperaturecooled to 0° C.
customThe resultant precipitate was collected by flirtation

Sources & evidence

ORD record: ord-55f511a55d61454a83be8c226edee531
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728829

Linked notes

Loading…