HCID 69430639, compound → HCID 69434560, compound

HRID 1269910Notes

Reaction equation

HRID 1269910 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:7][CH2:6][C@@H:5]([O:8][C:9]2[C:10]([CH3:18])=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[CH:12]3)[CH2:4][C@@H:3]1[N:19]1C(=O)C2C(=CC=CC=2)C1=O>CN.C(O)C>[CH3:1][C:2]1([CH3:30])[CH2:7][CH2:6][C@@H:5]([O:8][C:9]2[C:10]([CH3:18])=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[CH:12]3)[CH2:4][C@@H:3]1[NH2:19]

Participants

3

Reactant 1

HCID 69430639HCID 69430639, compound

Product 1

HCID 69434560HCID 69434560, compound

Reagents, catalysts & solvents 1

HCID 22028356Methylamine ethanolSolvent

Procedure

To trans-2-{2,2-dimethyl-5-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}-1H-isoindole-1,3(2H)-dione was added 30%-methylamine/ethanol (10 ml) at room temperature, and the resulting mixture was refluxed for 8 hours. The reaction solution was concentrated under reduced pressure at room temperature and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform→chloroform/methanol/(1%-aqueous ammonia)=20/1) to obtain trans-2,2-dimethyl-5-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanamine (143 mg, 60%, containing about 10% of cis isomer).

Workup

  1. temperaturethe resulting mixture was refluxed for 8 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure at room temperature
  3. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform→chloroform/methanol/(1%-aqueous ammonia)=20/1)

Sources & evidence

ORD record
ord-e19ce0d1a73a4183bbe2942321297358
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…