HCID 18355367, compound → HCID 18355027, compound

HRID 429685Notes

Reaction equation

HRID 429685 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]([NH:14][C:15]1[CH:46]=[CH:45][C:18]([C:19]([N:21]([CH3:44])[C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=3[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([N:37]3[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]3)=[O:36])=[O:20])=[CH:17][C:16]=1[O:47][CH3:48])=[O:13])[CH:8]=[CH:7][CH:6]=2>ClCCl.[O-2].[Mn+4].[O-2]>[CH:2]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]([NH:14][C:15]1[CH:46]=[CH:45][C:18]([C:19]([N:21]([CH3:44])[C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=3[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([N:37]3[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]3)=[O:36])=[O:20])=[CH:17][C:16]=1[O:47][CH3:48])=[O:13])[CH:8]=[CH:7][CH:6]=2)=[O:1]

Participants

4

Reactant 1

HCID 18355367HCID 18355367, compound

Product 1

HCID 18355027HCID 18355027, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[(2-hydroxymethylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (295 mg) in dichloromethane (8.0 ml) was added manganese(IV) oxide (196 mg) and the mixture was stirred at ambient temperature for 3 hours. The resulting mixture was filtered through a bed of celite and the filtrate was concentrated in vacuo. The residue was triturated with diethyl ether-n-hexane (1:3) to give 4-[(2-formylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (255 mg).

Workup

  1. filtrationThe resulting mixture was filtered through a bed of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was triturated with diethyl ether-n-hexane (1:3)

Sources & evidence

ORD record
ord-bbb7f90791524e16b89ff3e2763873cd
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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