HCID 57298719, compound → HCID 18354813, compound

HRID 1533761Notes

Reaction equation

HRID 1533761 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[C:54]([O:56][CH2:57][CH3:58])=[O:55])=O)(C)(C)C>FC(F)(F)C(O)=O>[CH2:57]([O:56][C: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)=[O:55])[CH3:58]

Participants

3

Reactant 1

HCID 57298719HCID 57298719, compound

Product 1

HCID 18354813HCID 18354813, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The mixture of 4-[(1-tert-butoxycarbonyl-2-ethoxycarbonylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (75 mg) in trifluoroacetic acid (2.0 ml) was stirred at ambient temperature for 5 minutes. Trifluoroacetic acid was removed in vacuo and the residue was diluted with aqueous saturated sodium bicarbonate solution. The solution was extracted with ethyl acetate and the organic layer was washed with brine. Drying, filtering and removal of solvents afforded 4-[(2-ethoxycarbonylindol-4-yl)-carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (50 mg) as a yellow amorphous powder.

Workup

  1. customTrifluoroacetic acid was removed in vacuo
  2. additionthe residue was diluted with aqueous saturated sodium bicarbonate solution
  3. extractionThe solution was extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. customDrying
  6. filtrationfiltering
  7. customremoval of solvents

Sources & evidence

ORD record
ord-c9f66645d6104d03abfe13ab01855021
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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