Water → HCID 178450517, compound

HRID 2289776Notes

Reaction equation

FC(F)(F)C(O)=O.ClC1C2C(=CC(C(NC(C(O)=O)CO)=O)=CC=2)C(NC(N)=N)=NC=1.Cl.[NH2:33][C:34]([NH2:36])=[NH:35].[C:37]([O:41][C:42](=[O:65])[CH:43]([CH2:59][O:60][C:61]([CH3:64])([CH3:63])[CH3:62])[NH:44][C:45]([C:47]1[CH:56]=[C:55]2[C:50]([C:51]([Cl:58])=[CH:52][N:53]=[C:54]2Cl)=[CH:49][CH:48]=1)=[O:46])([CH3:40])([CH3:39])[CH3:38].O>CS(C)=O>[C:37]([O:41][C:42](=[O:65])[CH:43]([CH2:59][O:60][C:61]([CH3:64])([CH3:63])[CH3:62])[NH:44][C:45]([C:47]1[CH:56]=[C:55]2[C:50]([C:51]([Cl:58])=[CH:52][N:53]=[C:54]2[NH:35][C:34]([NH2:36])=[NH:33])=[CH:49][CH:48]=1)=[O:46])([CH3:40])([CH3:39])[CH3:38]

Participants

Conditions

Temperature: 80 °C

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)carbonyl]-DL-serine trifluoroacetate ##STR72## NaH (54 mg, 80% dispersion in mineral oil, 1.80 mmol) was added to a solution of guanidine hydrochloride (173 mg, 1.81 mmol) in DMSO (6 mL) and the solution was heated to 80° C. for 30 min. O-t-Butyl-N-[(1,4-dichloro-7-isoquinolinyl)carbonyl]-DL-serine t-butyl ester (330 mg, 0.70 mmol) was added and the mixture heated at 80° C. for 3 h. The cooled mixture was poured into water (50 mL) and extracted with EtOAc. The combined organic extracts were washed with water, brine, dried (Na2SO4) and evaporated in vacuo. The residue was crystallised with i-Pr2O to give O-t-butyl-N-[(4-chloro-1-guanidino-7-isoquinolinyl)carbonyl]-DL-serine t-butyl ester (138 mg, 0.30 mmol) as a yellow solid.

Workup

temperaturethe mixture heated at 80° C. for 3 h
extractionextracted with EtOAc
washThe combined organic extracts were washed with water, brine
dry with materialdried (Na2SO4)
customevaporated in vacuo
customThe residue was crystallised with i-Pr2O

Sources & evidence

ORD record: ord-a25252f32c8d4e50957e57894e5c351d
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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