Hydrochloric Acid → HCID 25057343, compound

HRID 2423137Notes

Reaction equation

HRID 2423137 reaction equation
[H-].[Na+].[CH2:3]1[C:9]2=[C:10]3[C:14](=[CH:15][CH:16]=[C:8]2[O:7][CH2:6][CH2:5][N:4]1C(OC(C)(C)C)=O)[NH:13][CH:12]=[CH:11]3.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=1[S:33](Cl)(=[O:35])=[O:34].Cl>CN(C=O)C.O.C(Cl)Cl.C(OCC)C>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=1[S:33]([N:13]1[C:14]2[C:10](=[C:9]3[CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]3=[CH:16][CH:15]=2)[CH:11]=[CH:12]1)(=[O:34])=[O:35]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1451496-Methoxy-m-toluenesulfonyl chlorideHCID 67242130HCID 67242130, compound2×

Product 1

HCID 25057343HCID 25057343, compoundYield 83.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium hydride (60% in mineral oil, 16.6 mg, 0.312 mmol) was added to a solution of tert-butyl 1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 18, 0.060 g, 0.21 mmol) in DMF (3 mL). The mixture was stirred for 20 minutes at room temperature before (2-methoxy-5-methylphenyl)sulfonyl chloride (69 mg, 0.31 mmol) was added. The mixture was stirred for 20 minutes and diluted with water and DCM. The aqueous phase was adjusted to pH 3 with 1 M HCl and extracted with DCM (2×). The combined organics were evaporated to approximately 5 mL. TFA (2 mL) was added and the mixture was stirred at room temperature for 3 hours and the reaction mixture was evaporated. The residue was dissolved in DCM and triethylamine (1 mL) was added and the mixture was evaporated. The crude product was purified by flash chromatography on silica gel using MeOH:DCM:NEt3 (3:96:1) as the eluent to give a white solid which was suspended in diethylether and filtered. The white powder was washed with cold diethylether (2×) and dried in vacuo to give the title compound (65 mg). MS m/z 373 [M+H]+.

Workup

  1. additionwas added
  2. extractionextracted with DCM (2×)
  3. customThe combined organics were evaporated to approximately 5 mL
  4. additionTFA (2 mL) was added
  5. stirringthe mixture was stirred at room temperature for 3 hours
  6. customthe reaction mixture was evaporated
  7. dissolutionThe residue was dissolved in DCM
  8. additiontriethylamine (1 mL) was added
  9. customthe mixture was evaporated
  10. customThe crude product was purified by flash chromatography on silica gel
  11. customto give a white solid which
  12. filtrationfiltered
  13. washThe white powder was washed with cold diethylether (2×)
  14. customdried in vacuo

Sources & evidence

ORD record
ord-2d8047360fdb46ab9899744042ee124c
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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