Triethylamine → HCID 44407270, compound

HRID 2386168Notes

Reaction equation

HRID 2386168 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:16].BrCCCCN1C2C(=CC=CC=2)CCC1=O.[C:33]([C:37]1[N:42]=[C:41]([N:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH:40]=[C:39]([C:49]([F:52])([F:51])[F:50])[N:38]=1)([CH3:36])([CH3:35])[CH3:34].CCN(CC)CC>CN(C)C=O.C(OCC)(=O)C>[C:33]([C:37]1[N:42]=[C:41]([N:43]2[CH2:44][CH2:45][N:46]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:9][CH2:8][C:7]3=[O:16])[CH2:47][CH2:48]2)[CH:40]=[C:39]([C:49]([F:50])([F:51])[F:52])[N:38]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 129923681-(4-Bromobutan-1-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 183996102-(tert-Butyl)-4-(piperazin-1-yl)-6-(trifluoromethyl)pyrimidineHCID 204697121-(4-chlorobutyl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 44407270HCID 44407270, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-chlorobutyl)-3,4-dihydroquinolin-2(1H)-one and 1-(4-bromobutyl)-3,4-dihydroquinolin-2(1H)-one (0.30 g), 2-tert-butyl-4-piperazin-1-yl-6-(trifluoromethyl)-pyrimidine (1.08 mmol, 0.31 g; prepared as in DE 19735410) and NEt3 (4.54 mmol, 0.46 g) in N,N-dimethylformamide (10 ml) was heated at 100° C. while stirring for 20 hours. The reaction mixture was allowed to cool, ethyl acetate was added, and the reaction mixture was washed twice with water. The combined organic phases were dried over Na2SO4, the desiccant was filtered off, and the organic phase was concentrated in vacuo. The resulting oily residue was purified by chromatography on silica gel (eluent: methyl tert-butyl ether:methanol 0-100%), resulting in 0.17 g of the title compound.

Workup

  1. temperatureto cool
  2. washthe reaction mixture was washed twice with water
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationthe desiccant was filtered off
  5. concentrationthe organic phase was concentrated in vacuo
  6. customThe resulting oily residue was purified by chromatography on silica gel (eluent: methyl tert-butyl ether:methanol 0-100%)

Sources & evidence

ORD record
ord-0f4fc2520ce743818cf3cc41cdcc70e2
Source dataset
uspto-grants-2012_09
Patent number
US08268815B2

Reaction notes

Loading…