Guanidine Hydrochloride → HCID 178451234, compound

HRID 2289778Notes

Reaction equation

Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[C:6]([O:10][C:11](=[O:34])[CH2:12][N:13]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19]([Cl:26])=[CH:20][N:21]=[C:22]2Cl)=[CH:17][CH:16]=1)([CH3:9])([CH3:8])[CH3:7]>CC(O)(C)C>[C:6]([O:10][C:11](=[O:34])[CH2:12][N:13]([CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19]([Cl:26])=[CH:20][N:21]=[C:22]2[NH:4][C:3]([NH2:5])=[NH:2])=[CH:17][CH:16]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

Conditions

Temperature: 50 °C

Procedure

N-Benzyl-N-[(4-chloro-1-guanidino-7-isoquinolinyl)methyl]glycine bistrifluoroacetate ##STR76## NaH (48.6 mg, 80% dispersion in mineral oil, 1.62 mmol) was added to t-BuOH (5 mL) and heated to 50° C. for 15 min. Guanidine hydrocloride (155 mg, 1.62 mmol) was added and heated at 50° C. for an additional 20 min. N-Benzyl-N-[(1,4-dichloro-7-isoquinolinyl)methyl]glycine t-butyl ester (40 mg, 0.09 mmol) added and the mixture was then heated at 95° C. for 20 h. The cooled mixture was evaporated in vacuo and the residue purified by column chromatography on silica gel using CH2Cl2 -MeOH-0.880NH3 (95:5:0.5), followed by trituration with hexane and crystallisation with i-Pr2O, to give N-benzyl-N-[(4-chloro-1-guanidino-7-isoquinolinyl)methyl]glycine t-butyl ester (5 mg, 0.01 mmol) as a white solid.

Workup

temperatureheated at 50° C. for an additional 20 min
temperaturethe mixture was then heated at 95° C. for 20 h
customThe cooled mixture was evaporated in vacuo
customthe residue purified by column chromatography on silica gel
custom880NH3 (95:5:0.5), followed by trituration with hexane and crystallisation with i-Pr2O

Sources & evidence

ORD record: ord-30d34f92abfc47e6a7384fe5fa4b3af8
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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