1,3-Cyclohexanedione, 2-acetyl-5,5-dimethyl- → 1-(1-Amino-4-bromo-isoquinolin-6-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indazol-4-one

HRID 2244071Notes

Reaction equation

HRID 2244071 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][NH2:13])[CH:10]=2)[C:5]([NH2:14])=[N:4][CH:3]=1.[C:15]([CH:18]1[C:23](=[O:24])[CH2:22][C:21]([CH3:26])([CH3:25])[CH2:20][C:19]1=O)(=O)[CH3:16]>CCO.C(O)(=O)C>[NH2:14][C:5]1[C:6]2[C:11](=[CH:10][C:9]([N:12]3[C:19]4[CH2:20][C:21]([CH3:25])([CH3:26])[CH2:22][C:23](=[O:24])[C:18]=4[C:15]([CH3:16])=[N:13]3)=[CH:8][CH:7]=2)[C:2]([Br:1])=[CH:3][N:4]=1

Participants

4

Reactant 2

HCID 5194481,3-Cyclohexanedione, 2-acetyl-5,5-dimethyl-HCID 250596924-Bromo-6-hydrazino-isoquinolin-1-ylamine

Product 1

HCID 250609801-(1-Amino-4-bromo-isoquinolin-6-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indazol-4-oneYield 80.6%

Reagents, catalysts & solvents 1

HCID 18476134Acetic acid ethanolSolvent

Procedure

A suspension of 4-Bromo-6-hydrazino-isoquinolin-1-ylamine (0.097 g, 0.38 mmol) and 2-acetyl-5,5-dimethyl-1,3-cyclohexanedione (0.074 g, 0.41 mmol) in EtOH/Acetic acid (3:1, 7 mL) is microwaved at 150° C. for 20 min. The solvent is evaporated and the residue is dried under vacuum. Purification of the crude material using a Biotage column (0-10% MeOH/CH2Cl2) afforded 0.1223 g (80%) of 1-(1-Amino-4-bromo-isoquinolin-6-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indazol-4-one. LC/MS m/z=400 [M+H]+.

Workup

  1. customis microwaved at 150° C. for 20 min
  2. customThe solvent is evaporated
  3. customthe residue is dried under vacuum
  4. customPurification of the crude material

Sources & evidence

ORD record
ord-1f050a28e0a14f89aa1c7243a6673f58
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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