Methanesulfonyl chloride → 5-Acetyl-1-(1,3-benzodioxol-5-yl)-8-[(methylsulfonyl)amino]-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamide

HRID 1348926Notes

Reaction equation

HRID 1348926 reaction equation
C(O)(=O)C.[C:5]([N:8]1[C:17]2[CH:16]=[CH:15][C:14]([NH2:18])=[CH:13][C:12]=2[C:11]2[N:19]([C:25]3[CH:33]=[CH:32][C:28]4[O:29][CH2:30][O:31][C:27]=4[CH:26]=3)[N:20]=[C:21]([C:22]([NH2:24])=[O:23])[C:10]=2[CH2:9]1)(=[O:7])[CH3:6].[CH3:34][S:35](Cl)(=[O:37])=[O:36]>N1C=CC=CC=1>[C:5]([N:8]1[C:17]2[CH:16]=[CH:15][C:14]([NH:18][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:13][C:12]=2[C:11]2[N:19]([C:25]3[CH:33]=[CH:32][C:28]4[O:29][CH2:30][O:31][C:27]=4[CH:26]=3)[N:20]=[C:21]([C:22]([NH2:24])=[O:23])[C:10]=2[CH2:9]1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 101388555-Acetyl-8-amino-1-(1,3-benzodioxol-5-yl)-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamide acetate

Product 1

HCID 210926345-Acetyl-1-(1,3-benzodioxol-5-yl)-8-[(methylsulfonyl)amino]-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamideYield 25%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title material from Example 17 step 6 (300 mg, 0.000767 mol) was dissolved in pyridine (5 mL), and to this solution was added methane sulfonyl chloride (88 mg, 0.000767 mol). The resulting solution was stirred at room temperature for 18 hours. The reaction was then concentrated in vacuo, and the resulting solids were triturated with water and the product was isolated by vacuum filtration. 88 mg. (MW=469.48, 25% yield). LC/MS m/z=470.3 (m+1).

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. customthe resulting solids were triturated with water
  3. customthe product was isolated by vacuum filtration

Sources & evidence

ORD record
ord-c7669cd4ad8b47339d06958ccba26e56
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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