Water → 10-Chloro-8-[(2-methoxy-5-methylphenyl)sulfonyl]-1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

HRID 2423204Notes

Reaction equation

HRID 2423204 reaction equation
[H-].[Na+].CO[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([S:12](Cl)(=[O:14])=[O:13])=[CH:7][CH:6]=1.[Cl:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]3[O:30][CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH:26]([CH3:38])[C:24]3=2)[NH:19][CH:18]=1.O.CN([CH:43]=[O:44])C>>[Cl:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]3[O:30][CH2:29][CH2:28][NH:27][CH:26]([CH3:38])[C:24]3=2)[N:19]([S:12]([C:8]2[CH:9]=[C:10]([CH3:11])[CH:5]=[CH:6][C:7]=2[O:44][CH3:43])(=[O:13])=[O:14])[CH:18]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 159153174-Methoxy-3-methylbenzene-1-sulfonyl chlorideHCID 67242395tert-Butyl 10-chloro-1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate2×

Product 1

HCID 5976318610-Chloro-8-[(2-methoxy-5-methylphenyl)sulfonyl]-1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

Procedure

Sodium hydride (60% in mineral oil, 18 mg, 0.74 mmol) was added to a solution of 6-methoxy-m-toluensulfonyl chloride (98.3 mg, 0.445 mmol) and tert-butyl 10-chloro-1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 43, 50.0 mg, 0.148 mmol) in DMF (2 mL) at room temperature. The mixture was stirred for 15 minutes before water (5 mL) was added and the aqueous layer was extracted with DCM. Most of the organic solvents were evaporated and the residue was dissolved in DCM (1 mL) and TFA (2 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes. Solvents were evaporated and the crude product was purified by preparative HPLC (Xterra C18, 10 mM NH4HCO3 (pH 10) —CH3CN) to give the title compound as a white solid (16.8 mg). MS m/z 421 [M+H]+.

Workup

  1. additionwas added
  2. extractionthe aqueous layer was extracted with DCM
  3. customMost of the organic solvents were evaporated
  4. dissolutionthe residue was dissolved in DCM (1 mL)
  5. additionTFA (2 mL) was added
  6. customSolvents were evaporated
  7. customthe crude product was purified by preparative HPLC (Xterra C18, 10 mM NH4HCO3 (pH 10) —CH3CN)

Sources & evidence

ORD record
ord-e786d71e62e5434883084345a0152e60
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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