Triethylamine → 1-(4-(4-(2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl)piperazin-1-yl)butyl)-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

HRID 2240618Notes

Reaction equation

HRID 2240618 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10](=[O:17])[CH2:9][CH2:8][C:7]1=[O:18].[C:19]([C:23]1[N:28]=[C:27]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:26]=[C:25]([C:35]([F:38])([F:37])[F:36])[N:24]=1)([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O>[C:19]([C:23]1[N:28]=[C:27]([N:29]2[CH2:30][CH2:31][N:32]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[C:10](=[O:17])[CH2:9][CH2:8][C:7]3=[O:18])[CH2:33][CH2:34]2)[CH:26]=[C:25]([C:35]([F:36])([F:37])[F:38])[N:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 183996102-(tert-Butyl)-4-(piperazin-1-yl)-6-(trifluoromethyl)pyrimidineHCID 685828961-(4-chlorobutyl)-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

Product 1

HCID 112376641-(4-(4-(2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl)piperazin-1-yl)butyl)-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Chlorobutyl)-3,4-dihydro-1H-1-benzazepine-2,5-dione (3.29 mmol, 1.75 g, 70%), 2-tert-butyl-4-piperazin-1-yl-6-(trifluoromethyl)pyrimidine (3.56 mmol, 1.03 g; preparation according to WO 99/02503) and triethylamine (13.17 mmol, 1.33 g) in dimethylformamide (100 ml) were stirred at 100° C. for 12 h. Afterward, ethyl acetate was added and the mixture was washed twice with water. The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The oily residue was purified by chromatography on silica gel (eluent: 95:5 v/v dichloromethane:methanol); yield 0.42 g.

Workup

  1. washthe mixture was washed twice with water
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe oily residue was purified by chromatography on silica gel (eluent: 95:5 v/v dichloromethane:methanol)

Sources & evidence

ORD record
ord-4d80c3045ad24eba800debbc36eac546
Source dataset
uspto-grants-2010_05
Patent number
US07723384B2

Reaction notes

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