Methanesulfonyl chloride → HCID 59737229, compound

HRID 1907764Notes

Reaction equation

HRID 1907764 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:36]=[CH:35][C:10]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH:17]=[CH:18][C:19]=3[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.[CH3:37][S:38](Cl)(=[O:40])=[O:39].C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:34][C:31]1[CH:30]=[CH:29][C:28]([C:16]2[CH:17]=[CH:18][C:19]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:14]([NH:13][C:11](=[O:12])[C:10]3[CH:9]=[CH:8][C:7]([N:4]4[CH2:5][CH2:6][C@@H:2]([NH:1][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:3]4)=[CH:36][CH:35]=3)[CH:15]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 59737269HCID 59737269, compound

Product 1

HCID 59737229HCID 59737229, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of compound 404 (420 mg, 0.856 mmol) in DCM (2 mL) was cooled down to 0° C. and treated with neat methanesulfonyl chloride (148 mg, 1.29 mmol). The mixture was allowed to warm up to room temperature for 18 h. Cooled down to 0° C., treated with sat. NaHCO3 (1 mL), stirred for 1.5 h, diluted with DCM, washed with sat NaHCO3, dried over MgSO4 and concentrated under vacuum to afford the title compound 405 as a brown solid (430 mg, 88%) which was used without further purification

Workup

  1. temperatureCooled down to 0° C.
  2. washwashed
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-459afd332af64966b1db1e4b8d211ca1
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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