Pyridine-3-sulfonyl chloride hydrochloride → HCID 59513572, compound

HRID 1159858Notes

Reaction equation

HRID 1159858 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:12][N:13]([CH3:15])[CH3:14])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.Cl.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([S:23](Cl)(=[O:25])=[O:24])[CH:18]=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:23]([C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1)(=[O:25])=[O:24])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 59513572HCID 59513572, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(5-methoxy-1H-indol-4-yl)-N,N-dimethylmethanamine (30 mg, 0.15 mmol; Intermediate 97) and pyridine-3-sulfonyl chloride hydrochloride (43 mg, 0.20 mmol) in DCM (1 mL) 5 M NaOH (2 mL) was added. The reaction mixture was stirred at rt over night. The organic phase was collected and the solvent was removed under reduced pressure. Purification by preparative HPLC/UV (System B) afforded the title product (2 mg, 4%) as a white solid. MS (ESI+) for C17H19N3O3S m/z 346 (M+H)+.

Workup

  1. customThe organic phase was collected
  2. customthe solvent was removed under reduced pressure
  3. customPurification by preparative HPLC/UV (System B)

Sources & evidence

ORD record
ord-951d0908a8244d558858c1053699e1ef
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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