Acetyl chloride → HCID 178475373, compound

HRID 1526133Notes

Reaction equation

HRID 1526133 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Br.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:22]3[C:21](=[O:23])[NH:20][C:19]4[CH:24]=[C:25]([N:28]5[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)[CH:26]=[CH:27][C:18]=4[C:17]=3[C:16]3[C:34]([CH3:37])=[N:35][NH:36][C:15]=3[N:14]=2)=[CH:9][CH:8]=1>C1COCC1>[C:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:22]3[C:21](=[O:23])[NH:20][C:19]4[CH:24]=[C:25]([N:28]5[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)[CH:26]=[CH:27][C:18]=4[C:17]=3[C:16]3[C:34]([CH3:37])=[N:35][NH:36][C:15]=3[N:14]=2)=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178419526HCID 178419526, compound

Product 1

HCID 178475373HCID 178475373, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

132 μl (1.84 mmol, 145 mg) of acetyl chloride is added in several portions to a suspension of 602 mg (1.18 mmol) of 5-(4-hydroxyphenyl)-1-methyl-9-(piperazin-1-yl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one hydrobromide in 120 ml of THF at 0° C. The mixture is then stirred for 48 hours at room temperature and then concentrated under reduced pressure. The residue is purified by reverse-phase preparative HPLC to yield 51 mg (8%) of 4-(1-methyl-6-oxo-9-(piperazin-1-yl)-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-5-yl)phenyl acetate in the form of a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-992f7b61b0534ac7898998e3b966654d
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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