Dimethyl Sulfoxide → HCID 178476601, compound

HRID 1877441Notes

Reaction equation

HRID 1877441 reaction equation
OO.[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([C:24]4[NH:28][C:27]5[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:26]=5[N:25]=4)[C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:7][C:6]=1[NH:34][C@H:35]1[CH2:40][CH2:39][C@H:38]([O:41][C:42](=[O:44])[CH3:43])[CH2:37][CH2:36]1)#[N:4].CS(C)=[O:47].[OH-].[Na+]>C(O)C.O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([C:24]4[NH:28][C:27]5[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:26]=5[N:25]=4)[C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:7][C:6]=1[NH:34][C@H:35]1[CH2:36][CH2:37][C@H:38]([O:41][C:42](=[O:44])[CH3:43])[CH2:39][CH2:40]1)(=[O:47])[NH2:4]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 178476600HCID 178476600, compound

Product 1

HCID 178476601HCID 178476601, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a 50 ml three-necked flask, 1.36 ml of 30% aqueous hydrogen peroxide are added to a mixture of 200 mg of acetic acid 4-{2-cyano-5-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]phenylamino}-trans-cyclohexyl ester, obtained in the preceding stage, in 7.5 ml of ethanol and 3 ml of dimethyl sulphoxide and 0.96 ml of 1M sodium hydroxide, and the mixture is stirred for ¼ hour at ambient temperature. 40 ml of distilled water are added and the mixture is extracted with 3 times 40 ml of ethyl acetate. The combined organic phases are washed with twice 40 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and evaporated to dryness under vacuum. The residue is chromatographed on silica gel (15-40 μm), elution being carried out with a mixture of dichloromethane and methanol (96/4 by volume). 170 mg of acetic acid 4-{2-carbamoyl-5-[4-(6-fluoro-1H-benzimidazol-2-yl)-9H-carbazol-9-yl]phenylamino}-trans-cyclohexyl ester are obtained in the form of an off-white solid, the characteristics of which are the following:

Workup

  1. extractionthe mixture is extracted with 3 times 40 ml of ethyl acetate
  2. washThe combined organic phases are washed with twice 40 ml of a saturated solution of sodium chloride
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness under vacuum
  5. customThe residue is chromatographed on silica gel (15-40 μm), elution
  6. additionbeing carried out with a mixture of dichloromethane and methanol (96/4 by volume)

Sources & evidence

ORD record
ord-5c0ebc1e67c74e64a1319be414ab156d
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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