HCID 57298719, compound → HCID 18354813, compound

HRID 429634Notes

Reaction equation

HRID 429634 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-1ae33371b77b42f18014c91211e0ce3d
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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