Triethylamine → HCID 14278969, compound

HRID 868167Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[N:8][C:7]([C:15]([OH:17])=O)=[CH:6]2.C(N(CC)CC)C.P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[NH2:42][N:43]1[CH2:47][CH2:46][NH:45][C:44]1=[O:48]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[N:8][C:7]([C:15]([NH:42][N:43]1[CH2:47][CH2:46][NH:45][C:44]1=[O:48])=[O:17])=[CH:6]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6,7-dimethoxy-3-isoquinolinecarboxylic acid (6.99 g, 30.0 mmol) in 300 ml of N,N-dimethylformamide were added triethylamine (12.14 g, 120.0 mmol) and diphenyl chlorophosphate (80.6 g, 30.0 mmol) at 0° C. After stirring for 4 hours at 0° C., N-amino-2-oxoimidazolidine (3.03 g, 30.0 mmol) was added, and the mixture was stirred at 0° C. overnight. Ammonium salts (2.0 g) were filtered off, and the filtrate was evaporated in vacuo. The residue was triturated with a 1:1 mixture of water and ethyl acetate. The solid was filtered off and triturated twice with water at pH 8 for 3 hours. The remaining solid was filtered off, washed with water and dried in vacuo. Yield: 4.30 g; melting point 220° C. (dec.).

Workup

stirringthe mixture was stirred at 0° C. overnight
filtrationAmmonium salts (2.0 g) were filtered off
customthe filtrate was evaporated in vacuo
customThe residue was triturated with a 1:1 mixture of water and ethyl acetate
filtrationThe solid was filtered off
customtriturated twice with water at pH 8 for 3 hours
filtrationThe remaining solid was filtered off
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-e31d235e44014bf1835f60c00cdd98e8
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04777252

Reaction notes

Loading…