Dimethylformamide → HCID 59513545, compound

HRID 1159852Notes

Reaction equation

HRID 1159852 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.CN(C=O)C.[N:21]1[S:22][N:23]=[C:24]2[C:29]([S:30](Cl)(=[O:32])=[O:31])=[CH:28][CH:27]=[CH:26][C:25]=12>>[N:21]1[S:22][N:23]=[C:24]2[C:29]([S:30]([N:8]3[C:9]4[C:5](=[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])[C:3]([O:2][CH3:1])=[CH:11][CH:10]=4)[CH:6]=[CH:7]3)(=[O:32])=[O:31])=[CH:28][CH:27]=[CH:26][C:25]=12

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 27354592,1,3-Benzothiadiazole, 4-chlorosulfonyl-HCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 59513545HCID 59513545, compoundYield 11%

Procedure

To a solution of 1-(5-methoxy-11H-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 2,1,3-benzothiadiazole-4-sulfonyl chloride (26 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 (3 mg, 11%) as a yellow solid. MS (ESI+) for C18H18N4O3S2 m/z 403 (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-566f20cd2bc94ba3be9b52603974993a
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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