Benzenesulfonyl chloride → HCID 67241199, compound

HRID 2423130Notes

Reaction equation

HRID 2423130 reaction equation
[H-].[Na+].[F:3][C:4]([F:9])([F:8])[C:5]([OH:7])=[O:6].[CH3:10][N:11]1[CH2:25][C:16]2=[C:17]3[C:21](=[C:22]([CH3:24])[CH:23]=[C:15]2[O:14][CH2:13][CH2:12]1)[NH:20][CH:19]=[CH:18]3.[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[F:3][C:4]([F:9])([F:8])[C:5]([OH:7])=[O:6].[CH3:10][N:11]1[CH2:25][C:16]2=[C:17]3[C:21](=[C:22]([CH3:24])[CH:23]=[C:15]2[O:14][CH2:13][CH2:12]1)[N:20]([S:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:34])=[O:33])[CH:19]=[CH:18]3

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 67241493HCID 67241493, compound2×

Product 1

HCID 67241199HCID 67241199, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 14 mg, 0.54 mmol, 95%) was added to a solution of 2,7-dimethyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole trifluoroacetate (Intermediate 13, 0.060 g, 0.18 mmol) in DMF (2 mL) and stirred at room temperature for 5 minutes before benzenesulfonyl chloride (0.035 mL, 0.27 mmol) was added. The mixture was stirred at room temperature for 10 minutes and quenched with ice/water and extracted with DCM. The crude material was purified by preparative HPLC (ACE C8, 0.1% TFA-CH3CN) to give the title compound as a brown oil (14 mg) in the form of the trifluoroacetate salt. MS m/z 357 [M+H]+.

Workup

  1. additionwas added
  2. customquenched with ice/water
  3. extractionextracted with DCM
  4. customThe crude material was purified by preparative HPLC (ACE C8, 0.1% TFA-CH3CN)

Sources & evidence

ORD record
ord-60cc3136039f49cf83752352daa858b8
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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