Dimethylformamide → HCID 59513565, compound

HRID 1159853Notes

Reaction equation

HRID 1159853 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.[O:21]1[C:27]2[CH:28]=[CH:29][C:30]([S:32](Cl)(=[O:34])=[O:33])=[CH:31][C:26]=2[O:25][CH2:24][CH2:23][CH2:22]1>>[O:21]1[C:27]2[CH:28]=[CH:29][C:30]([S:32]([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:34])=[O:33])=[CH:31][C:26]=2[O:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 27763863,4-dihydro-2H-1,5-benzodioxepine-7-sulfonyl chlorideHCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

HCID 59513565HCID 59513565, compoundYield 17.2%

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 3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonyl chloride (27 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 (5 mg, 17%) as a yellow solid. MS (ESI+) for C21H24N2O5S m/z 417 (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-9d8b7831e13e479bbc9d20ebf784c79d
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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