Guanidine Hydrochloride → HCID 178470306, compound

HRID 2289766Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([NH:14][C:15]3([C:20]([OH:22])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:13])=[CH:9][CH:10]=2)[C:5]([NH:23][C:24]([NH2:26])=[NH:25])=[N:4][CH:3]=1.Cl.NC(N)=N.[CH2:32](OC(=O)C1(CCCC1)NC(C1C=C2C(C(Cl)=CN=C2Cl)=CC=1)=O)[CH3:33]>CC(O)(C)C>[CH2:32]([O:21][C:20](=[O:22])[C:15]1([CH2:19][CH2:18][CH2:17][CH2:16]1)[NH:14][C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2]([Cl:1])=[CH:3][N:4]=[C:5]2[NH:23][C:24]([NH2:26])=[NH:25])=[CH:10][CH:9]=1)=[O:13])[CH3:33]

Participants

Conditions

Temperature: 50 °C

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)carbonyl]cycloleucine ##STR62## NaH (45 mg, 60% dispersion in mineral oil, 1.13 mmol) was added to t-BuOH and the mixture heated at 50° C. for 15 min. Guanidine hydrochloride (105 mg, 1.10 mmol) was added and the mixture heated at 50° C. for an additional 15 min. N-[(1,4-Dichloro-7-isoquinolinyl)carbonyl]cycloleucine ethyl ester (350 mg, 0.92 mmol) was added and the mixture heated at reflux for 17 h. The solvents were evaporated in vacuo and the residue purified by column chromatography on silica gel using CH2Cl2 -MeOH-0.880NH3 (90:10:1) as eluant, followed by trituration with CH2Cl2 -i-Pr2O, to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)carbonyl]cycloleucine ethyl ester (55 mg, 0.14 mmol) as a pale yellow powder.

Workup

temperaturethe mixture heated at 50° C. for an additional 15 min
temperaturethe mixture heated
temperatureat reflux for 17 h
customThe solvents were evaporated in vacuo
customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-77215f7b92a44d27b06f3957b5ee79bd
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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