Water → HCID 178450909, compound

HRID 2289771Notes

Reaction equation

FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([NH:21][CH:22]([C:30]([OH:32])=[O:31])[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:20])=[CH:16][CH:17]=2)[C:12]([NH:33][C:34]([NH2:36])=[NH:35])=[N:11][CH:10]=1.Cl.NC(N)=N.[C:42](OC(=O)C(CC1C=CC=CC=1)NC(C1C=C2C(C(Cl)=CN=C2Cl)=CC=1)=O)([CH3:45])([CH3:44])[CH3:43].O>CS(C)=O>[C:42]([O:31][C:30](=[O:32])[CH:22]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:21][C:19]([C:15]1[CH:14]=[C:13]2[C:18]([C:9]([Cl:8])=[CH:10][N:11]=[C:12]2[NH:33][C:34]([NH2:36])=[NH:35])=[CH:17][CH:16]=1)=[O:20])([CH3:45])([CH3:44])[CH3:43]

Participants

Conditions

Temperature: 80 °C

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)carbonyl]-DL-phenylalanine trifluoroacetate ##STR68## NaH (78 mg, 60% dispersion in mineral oil, 1.95 mmol) was added to a solution of guanidine hydrochloride (188 mg, 1.97 mmol) in DMSO (6 mL) at 50° C. and the solution was stirred for 15 min. N-[(1,4-Dichloro-7-isoquinolinyl)carbonyl]-DL-phenylalanine t-butyl ester (350 mg, 0.79 mmol) was added and the mixture heated at 80° C. overnight. The cooled mixture was poured into water (50 mL) and extracted with EtOAc (2×25 mL). The combined organics were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was crystallised with CH2Cl2 -i-Pr2O to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)carbonyl]-DL-phenylalanine t-butyl ester (172 mg, 0.37 mmol) as a cream coloured solid.

Workup

extractionextracted with EtOAc (2×25 mL)
washThe combined organics were washed with brine
dry with materialdried (Na2SO4)
customevaporated in vacuo
customThe residue was crystallised with CH2Cl2 -i-Pr2O

Sources & evidence

ORD record: ord-d06a32d4b01f4265850adcc568ca7a3e
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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