Methyl iodide → HCID 22291947, compound

HRID 968139Notes

Reaction equation

HRID 968139 reaction equation
[C:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:22]3[C:21]4[CH:23]=[C:24]([NH:27][C:28](=[O:36])[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[Cl:35])[CH:25]=[CH:26][C:20]=4[CH2:19][CH2:18][C:17]=3[C:16]([C:37]([NH2:39])=[O:38])=[N:15]2)=[CH:10][CH:9]=1)(=[O:7])=[O:6])(=[O:3])[CH3:2].I[CH3:41]>CN(C=O)C>[Cl:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:28]([NH:27][C:24]1[CH:25]=[CH:26][C:20]2[CH2:19][CH2:18][C:17]3[C:16]([C:37]([NH2:39])=[O:38])=[N:15][N:14]([C:11]4[CH:10]=[CH:9][C:8]([S:5]([NH:4][CH3:1])(=[O:6])=[O:7])=[CH:13][CH:12]=4)[C:22]=3[C:21]=2[CH:23]=1)=[O:36].[C:1]([N:4]([CH3:41])[S:5]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:22]3[C:21]4[CH:23]=[C:24]([NH:27][C:28](=[O:36])[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[Cl:35])[CH:25]=[CH:26][C:20]=4[CH2:19][CH2:18][C:17]=3[C:16]([C:37]([NH2:39])=[O:38])=[N:15]2)=[CH:12][CH:13]=1)(=[O:7])=[O:6])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 22291714HCID 22291714, compound

Product 2

HCID 22291544HCID 22291544, compoundHCID 22291947HCID 22291947, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirring solution of 1-{4-[(acetylamino)sulfonyl]phenyl}-8-[(2-chlorobenzoyl)amino]-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (563 mg, 1 mmol) in DMF (20 mL) was added NaH2 (40 mg, 1 mmol). The mixture was stirred at room temperature for 1 h. To the mixture was added a solution of Iodomethane (170.3 mg, 1.2 mmol) in DMF (1 mL). The solution was stirred at room temperature for 4 h and concentrated. It was purified by HPLC to give a solid of the desired compound 1-(4-{[acetyl(methyl)amino]sulfonyl}phenyl)-8-[(2-chlorobenzoyl)amino]-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (155 mg, 27%.)

Workup

  1. stirringThe solution was stirred at room temperature for 4 h
  2. concentrationconcentrated
  3. customIt was purified by HPLC

Sources & evidence

ORD record
ord-8e7d29a4f923480385363c741ad24272
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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