Trifluoroacetic acid → HCID 86756563, compound

HRID 1533763Notes

Reaction equation

HRID 1533763 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[NH:35][C:36]([C:38]1[C:46]2[N:45]=[C:44]([C:47](=[O:50])[NH:48][CH3:49])[N:43](CC3C=CC(OC)=CC=3)[C:42]=2[CH:41]=[CH:40][CH:39]=1)=[O:37])[C:6]([N:8]([CH3:31])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](N1CCN(C)CC1)=[O:23])=[O:7].F[C:61](F)(F)[C:62](O)=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[NH:35][C:36]([C:38]1[C:46]2[N:45]=[C:44]([C:47](=[O:50])[NH:48][CH3:49])[NH:43][C:42]=2[CH:41]=[CH:40][CH:39]=1)=[O:37])[C:6]([N:8]([CH3:31])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[C:22]=[O:23])[N:45]1[CH2:62][CH2:61][N:43]([CH3:44])[CH2:42][CH2:46]1)=[O:7]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18354948HCID 18354948, compound

Product 1

HCID 86756563HCID 86756563, compound

Procedure

A solution of 3-methoxy-4-[1-(4-methoxybenzyl)-2-(N-methylcarbamoyl)-1 H-benzimidazol-4-yl]carbonylamino-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (130 mg) in trifluoroacetic acid (3 ml) was stirred at 60° C. for 8 hours. The reaction mixture was concentrated in vacuo and the residue was diluted with a mixture of chloroform and saturated aqueous sodium bicarbonate solution. The organic layer was separated and washed with water and brine. The solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1) to give 3-methoxy-N-methyl-4-[2-(N-methylcarbamoyl)-1 H-benzimidazol-4-yl]carbonylamino-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)-carbonylpent-1-yloxy]phenyl]benzamide (45 mg) as a powder.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with a mixture of chloroform and saturated aqueous sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1)

Sources & evidence

ORD record
ord-ec9458d6b54645359c05abd389a733b8
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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