Hydrochloric Acid → HCID 18398859, compound

HRID 1019400Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[C:17](=[O:19])[N:16]([C:20]1[CH:25]=[CH:24][C:23]([NH:26]C(OC(C)(C)C)=O)=[CH:22][CH:21]=1)[C:15]([C:34]([O:36][CH3:37])=[O:35])=[C:14]2[C:38]1[CH:43]=[C:42]([O:44][CH3:45])[C:41]([O:46][CH3:47])=[C:40]([O:48][CH3:49])[CH:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[NH2:26][C:23]1[CH:22]=[CH:21][C:20]([N:16]2[C:15]([C:34]([O:36][CH3:37])=[O:35])=[C:14]([C:38]3[CH:43]=[C:42]([O:44][CH3:45])[C:41]([O:46][CH3:47])=[C:40]([O:48][CH3:49])[CH:39]=3)[C:13]3[C:18](=[C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:10]=[CH:11][CH:12]=3)[C:17]2=[O:19])=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of the compound obtained in Example 335 (53 mg) in chloroform (4 ml) is cooled to 0° C., and thereto is added a 4M solution of hydrogen chloride in ethyl acetate (2 ml). The mixture is stirred at 0° C. for two hours, and thereto is added a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with ethyl acetate. The extract is washed, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=1:2) to give 2-(4-aminophenyl)-8-benzyloxy-3-methoxycarbonyl-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (20 mg) as listed in Table 30.

Workup

extractionthe mixture is extracted with ethyl acetate
washThe extract is washed
customdried
concentrationconcentrated under reduced pressure
customThe residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=1:2)

Sources & evidence

ORD record: ord-97adf70f661f4d68ae0a46cdcf049551
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06486155B1

Reaction notes

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