Water → HCID 178450718, compound

HRID 2289769Notes

Reaction equation

FC(F)(F)C(O)=O.N1CCCC1C(O)=O.Cl.[NH2:17][C:18]([NH2:20])=[NH:19].[C:21]([O:25][C:26](=[O:46])[CH:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:32]([C:34]1[CH:43]=[C:42]2[C:37]([C:38]([Cl:45])=[CH:39][N:40]=[C:41]2Cl)=[CH:36][CH:35]=1)=[O:33])([CH3:24])([CH3:23])[CH3:22].O>CS(C)=O>[C:21]([O:25][C:26](=[O:46])[CH:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:32]([C:34]1[CH:43]=[C:42]2[C:37]([C:38]([Cl:45])=[CH:39][N:40]=[C:41]2[NH:19][C:18]([NH2:20])=[NH:17])=[CH:36][CH:35]=1)=[O:33])([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

N-1(4-Chloro-1-guanidino-7-isoquinolinyl)carbonyl]-DL-proline trifluoroacetate ##STR67## NaH (65 mg, 60% dispersion in mineral oil, 1.63 mmol) was added to a stirred solution of guanidine hydrochloride (154 mg, 1.61 mmol) in DMSO (5 mL) at 50° C. and the solution stirred for 15 min. N-[(1,4-Dichloro-7-isoquinolinyl)carbonyl]-DL-proline t-butyl ester (253 mg, 0.64 mmol) was added and the mixture was heated at 80° C. overnight. The mixture was poured into water (20 mL) and extracted with EtOAc (×2). The combined organic extracts were washed with water, brine, dried over (MgSO4), and evaporated in vacuo. The residue was crystallised with CH2Cl2 -i-Pr2O to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)carbonyl]-DL-proline t-butyl ester (241 mg, 0.58 mmol).

Workup

extractionextracted with EtOAc (×2)
washThe combined organic extracts were washed with water, brine
dry with materialdried over (MgSO4)
customevaporated in vacuo
customThe residue was crystallised with CH2Cl2 -i-Pr2O

Sources & evidence

ORD record: ord-2a85286f2933449981254caa037ce8be
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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