HCID 18355314, compound → HCID 18355341, compound

HRID 429681Notes

Reaction equation

HRID 429681 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[C:12]([C:17]([NH:19][C:20]3[CH:51]=[CH:50][C:23]([C:24]([N:26]([CH3:49])[C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=4[O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([N:42]4[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]4)=[O:41])=[O:25])=[CH:22][C:21]=3[O:52][CH3:53])=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:54][N:55]1C(=O)C2=CC=CC=C2C1=O)=O)(C)(C)C>C(O)C.[OH-].[Na+].O>[NH2:55][CH2:54][C:9]1[NH:8][C:16]2[C:11]([CH:10]=1)=[C:12]([C:17]([NH:19][C:20]1[CH:51]=[CH:50][C:23]([C:24]([N:26]([CH3:49])[C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=3[O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([N:42]3[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]3)=[O:41])=[O:25])=[CH:22][C:21]=1[O:52][CH3:53])=[O:18])[CH:13]=[CH:14][CH:15]=2

Participants

5

Reactant 1

HCID 18355314HCID 18355314, compound

Product 1

HCID 18355341HCID 18355341, compoundYield 98.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

The solution of 4-[(1-tert-butoxycarbonyl-2-phthalimidomethylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (312 mg) in ethanol (5.0 ml) and 1N sodium hydroxide aqueous solution (1.76 ml) was stirred at ambient temperature for 6 hours. The resulting solution was diluted with water and extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 4-[(2-aminomethylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (228 mg).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4296690698be428ea9a222c51ec1930c
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

Loading…