Dimethyl Sulfoxide → HCID 18354940, compound

HRID 429643Notes

Reaction equation

HRID 429643 reaction equation
[OH:1][CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([NH:14][C:15]3[CH:46]=[CH:45][C:18]([C:19]([N:21]([CH3:44])[C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=4[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([N:37]4[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]4)=[O:36])=[O:20])=[CH:17][C:16]=3[O:47][CH3:48])=[O:13])[C:5]=2[N:4]=1.C(N(CC)CC)C.CS(C)=O.C(=O)(O)[O-].[Na+]>O.ClCCl>[CH:2]([C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([NH:14][C:15]3[CH:46]=[CH:45][C:18]([C:19]([N:21]([CH3:44])[C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=4[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([N:37]4[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]4)=[O:36])=[O:20])=[CH:17][C:16]=3[O:47][CH3:48])=[O:13])[C:5]=2[N:4]=1)=[O:1]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 18355140HCID 18355140, compound

Product 1

HCID 18354940HCID 18354940, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(2-hydroxymethyl-1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (40 mg), triethylamine (31 mg), dimethyl sulfoxide (0.5 ml) and dichloromethane (0.5 ml) was added portionwise sulfur trioxide pyridine complex (29 mg) in water bath and the mixture was stirred at the same temperature for 1 day. The reaction mixture was poured into saturated aqueous sodium bicarbonate solution and the solution was extracted with chloroform. The organic layer was washed with water and brine and the solution was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1) to give 4-(2-formyl-1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (6 mg) as a powder.

Workup

  1. extractionthe solution was extracted with chloroform
  2. washThe organic layer was washed with water and brine
  3. dry with materialthe solution was dried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1)

Sources & evidence

ORD record
ord-d707136f0c1c402bb3eb770e19fa1777
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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