Dichloromethane → HCID 22185472, compound

HRID 1795147Notes

Reaction equation

HRID 1795147 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][C:8]([C:11]1[NH:12][C:13]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([Cl:23])=[C:20](O)[CH:21]=2)[N:15]=1)([CH3:10])[CH3:9].[Cl:30]CCl>CO.C(=O)([O-])O.[Na+]>[Cl:30][C:20]1[CH:21]=[C:16]([C:14]2[N:15]=[C:11]([C:8]([CH3:10])([CH3:9])[CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[NH:12][C:13]=2[C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:17]=[CH:18][C:19]=1[Cl:23]

Participants

6

Reactant 3

HCID 6344Dichloromethane2×HCID 31297Methanesulfonyl chlorideHCID 22185475HCID 22185475, compound

Product 1

HCID 22185472HCID 22185472, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of methanesulfonyl chloride (33 mg, 0.3 mmol) in dichloromethane (4 ml) was treated with a solution of Example 3 (103 mg, 0.3 mmol) in methanol (1 ml). The mixture was stirred at room temperature for 2 hours then diluted with dichloromethane and sodium hydrogen carbonate solution. The aqueous layer was then separated and extracted with additional dichloromethane. The combined organic layers were then washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with dichloromethane/methanol/0.880 ammonia solution (10:1:0.1) to give the title compound (16 mg, 13%) as a pale yellow solid; MS(ES+) m/e 421/423 [M+H]+.

Workup

  1. customThe aqueous layer was then separated
  2. extractionextracted with additional dichloromethane
  3. washThe combined organic layers were then washed with brine
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with dichloromethane/methanol/0.880 ammonia solution (10:1:0.1)

Sources & evidence

ORD record
ord-efb5287d556c41b5bd508c28cf051c9b
Source dataset
uspto-grants-2006_04
Patent number
US07026336B1

Reaction notes

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