2-Chlorobenzyl chloride → 5-Acetyl-1-(1,3-benzodioxol-5-yl)-8-[(2-chlorobenzoyl)amino]-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamide

HRID 1348924Notes

Reaction equation

HRID 1348924 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[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].[Cl:34][C:35]1C=[CH:41][CH:40]=[CH:39][C:36]=1CCl>N1C=CC=CC=1>[C:5]([N:8]1[C:17]2[CH:16]=[CH:15][C:14]([NH:18][C:1](=[O:4])[C:2]3[CH:41]=[CH:40][CH:39]=[CH:36][C:35]=3[Cl:34])=[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 119062-Chlorobenzyl 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 103019985-Acetyl-1-(1,3-benzodioxol-5-yl)-8-[(2-chlorobenzoyl)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 (280 mg, 0.00072 mol) and 2-chlorobenzyl chloride (126 mg, 0.00072 mol, d=1.382 g/mol, 91 μL) were dissolved in pyridine (2 mL) and stirred for 4 hours. The pyridine was removed in vacuo and the resulting material was purified via HPLC to give the title compound. 95 mg (MW=529.93, 25% yield). LC/MS m/z=530.96 (m+1).

Workup

  1. customThe pyridine was removed in vacuo
  2. customthe resulting material was purified via HPLC

Sources & evidence

ORD record
ord-7c7d5dc851ea45d09882baa799ee63a8
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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