HCID 18354898, compound → HCID 18355132, compound

HRID 429684Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15]([NH:17][C:18]2[CH:49]=[CH:48][C:21]([C:22]([N:24]([CH3:47])[C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=3[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([N:40]3[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]3)=[O:39])=[O:23])=[CH:20][C:19]=2[O:50][CH3:51])=[O:16])[NH:7]1)=O)C.[NH3:52].CO>>[C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15]([NH:17][C:18]2[CH:49]=[CH:48][C:21]([C:22]([N:24]([CH3:47])[C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=3[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([N:40]3[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]3)=[O:39])=[O:23])=[CH:20][C:19]=2[O:50][CH3:51])=[O:16])[NH:7]1)(=[O:3])[NH2:52]

Participants

Reactant 2

HCID 18354898HCID 18354898, compound

HCID 21705897Ammonia methanol

Product 1

HCID 18355132HCID 18355132, compound

Procedure

The solution of 4-[(2-ethoxycarbonylindolin-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (175 mg) in ammonia-methanol solution (8.0 ml) was stood overnight at ambient temperature. The solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent; 8-10% methanol in chloroform) to give 4-[(2-carbamoylindolin-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (160 mg).

Workup

customThe solvent was evaporated in vacuo
customthe residue was purified by silica gel column chromatography (eluent; 8-10% methanol in chloroform)

Sources & evidence

ORD record: ord-bfabd9134a034370b97059435189bb60
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06316482B1

Reaction notes

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