Dimethylformamide → HCID 59513556, compound

HRID 1159842Notes

Reaction equation

HRID 1159842 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.[CH3:16]N(C=O)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](C)=[CH:24][C:23]=1[S:29](Cl)(=[O:31])=[O:30]>>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:16])[C:23]=1[S:29]([N:8]1[C:9]2[C:5](=[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])[C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1)(=[O:30])=[O:31]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 151553332-Chloro-5-methylbenzene-1-sulfonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 59513556HCID 59513556, compoundYield 25.5%

Procedure

To a solution of 1-(5-methoxy-1H-indol-4-yl)-N,N-dimethylmethanamine (15 mg, 0.07 mmol; Intermediate 97) in DMF (1 mL) NaH (4 mg, 0.15 mmol) was added at rt. The reaction mixture was stirred at rt for 15 min and 2-chloro-5-methylbenzene-1-sulfonyl chloride (25 mg, 0.11 mmol) was added. The reaction mixture was allowed to stir at rt over night. The reaction was quenched by addition of water. Purification by preparative HPLC/UV (System B) afforded the title product (7 mg, 24%) as a white solid. MS (ESI+) for C19H21ClN2O3S m/z 394 (M+H)+.

Workup

  1. stirringto stir at rt over night
  2. customThe reaction was quenched by addition of water
  3. customPurification by preparative HPLC/UV (System B)

Sources & evidence

ORD record
ord-18f54debcec54cc484bce0df1e8db82e
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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