Water → HCID 178451195, compound

HRID 2289780Notes

Reaction equation

FC(F)(F)C(O)=O.ClC1C2C(=CC(S(N[C@H](C(O)=O)CCC(=O)N)(=O)=O)=CC=2)C(NC(N)=N)=[N:11]C=1.Cl.[NH2:37][C:38]([NH2:40])=[NH:39].[C:41]([O:45][C:46](=[O:69])[C@H:47]([CH2:64][CH2:65][C:66](=[O:68])[NH2:67])[NH:48][S:49]([C:52]1[CH:61]=[C:60]2[C:55]([C:56]([Cl:63])=[CH:57][N:58]=[C:59]2Cl)=[CH:54][CH:53]=1)(=[O:51])=[O:50])([CH3:44])([CH3:43])[CH3:42].O>CS(C)=O>[NH3:11].[C:41]([O:45][C:46](=[O:69])[C@H:47]([CH2:64][CH2:65][C:66](=[O:68])[NH2:67])[NH:48][S:49]([C:52]1[CH:61]=[C:60]2[C:55]([C:56]([Cl:63])=[CH:57][N:58]=[C:59]2[NH:39][C:38]([NH2:40])=[NH:37])=[CH:54][CH:53]=1)(=[O:50])=[O:51])([CH3:44])([CH3:42])[CH3:43]

Participants

Conditions

Temperature: 50 °C

Procedure

N-[(4-Chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-glutamine trifluoroacetate ##STR79## NaH (25 mg, 80% dispersion in mineral oil, 0.83 mmol) was added to a solution of guanidine hydrochloride (128 mg, 1.34 mmol) in DMSO (2 ml) and stirred at 50° C. for 1 h. N-[(1,4-Dichloro-7-isoquinolinyl)sulphonyl]-L-glutamine tert-butyl ester (150 mg, 0.32 mmol) was added and the resultant solution stirred at 100° C. for 6 h, allowed to cool and then poured into water. The aqueous mixture was extracted with EtOAc (3×30 ml) and concentrated in vacuo. The residue was purified by column chromatography upon silica gel using CH2Cl2 -MeOH-0.880 NH3 (90:10:1) as eluant to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-glutamine tert-butyl ester (30 mg, 0.06 mmol) as a buff-coloured powder.

Workup

temperatureto cool
extractionThe aqueous mixture was extracted with EtOAc (3×30 ml)
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record: ord-696a1c3587384fb99cb93ad5c77f4f69
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093731

Reaction notes

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