8-Aminoquinoline → 1-(Quinolin-8-ylamino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-ol

HRID 2182636Notes

Reaction equation

HRID 2182636 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[NH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2>N1CCCNC1=O>[N:30]1[C:31]2[C:26](=[CH:25][CH:24]=[CH:23][C:22]=2[NH:21][CH2:12][C:10]([C:13]([F:16])([F:15])[F:14])([OH:11])[CH2:9][C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:19][CH3:20])([CH3:18])[CH3:17])[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Product 1

HCID 219488611-(Quinolin-8-ylamino)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentan-2-olYield 77.5%

Reagents, catalysts & solvents 1

HCID 746152(1H)-Pyrimidinone, tetrahydro-Solvent

Procedure

200 mg (0.68 mmol) of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl)-2-(trifluoromethyl)oxirane (WO 00/32584) and 99 mg (0.68 mmol) of 8-aminoquinoline are heated in 0.2 ml of 3,4,5,6-tetrahydro-2-(1H)-pyrimidone (DMPU) for 20 hours to 130° C. After the reaction mixture is purified on silica gel with hexane-ethyl acetate (0-20%), 230 mg of the product is obtained.

Workup

  1. customAfter the reaction mixture is purified on silica gel with hexane-ethyl acetate (0-20%)

Sources & evidence

ORD record
ord-ebcaf543ef084a0e9657b4732b0f978d
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

Loading…