Benzenesulfonyl chloride → HCID 25072815, compound

HRID 1096493Notes

Reaction equation

HRID 1096493 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14][CH2:15][C:5]([C:6]=23)=[CH:4]1.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[C:23]1([S:29]([N:3]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]4[CH2:12][NH:13][CH2:14][CH2:15][C:5]([C:6]=34)=[CH:4]2)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 59848834HCID 59848834, compound

Product 1

HCID 25072815HCID 25072815, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% in mineral oil, 66 mg, 0.4 mmol) was added to a solution of tert-butyl 1,3,4,6-tetrahydro-5H-azepino[5,4,3-cd]indole-5-carboxylate, Intermediate 12 (51 mg, 0.2 mmol) in 800 of dry DMF). The reaction mixture was shaken at room temperature for 10 minutes and phenylsulfonyl chloride (66.2 mg, 0.4 mmol, in 600 uL of dry DMF) was added. The reaction mixture was shaken at room temperature for 10-20 minutes. The reaction was quenched by adding 4 mL of mixture a mixture of methanol and acetic acid (1:1). Boc-deprotection was carried out by adding 4 mL of solution of TFA/DCM (1:1). 2M NH3 in MeOH was added to the crude reaction (2×10 mL) and the solvent was removed under vacuum. The crude product was purified by preparative HPLC using System B, 100 mM NH4HCO3/MeCN (10-50% MeCN). 50 mg of the pure product was isolated as an off-white solid. MS m/z 313 [M+H]+.

Workup

  1. stirringThe reaction mixture was shaken at room temperature for 10-20 minutes
  2. customThe reaction was quenched
  3. additionby adding 4 mL of mixture
  4. additiona mixture of methanol and acetic acid (1:1)
  5. additionby adding 4 mL of solution of TFA/DCM (1:1)
  6. addition2M NH3 in MeOH was added to the crude
  7. customreaction (2×10 mL)
  8. customthe solvent was removed under vacuum
  9. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-31b4bb8092f648dfab2b27ccbc4ff86c
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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