Diisopropylethylamine → 1-Acetyl-6-([2,4-difluorobenzylamino]methylcarbonyl)amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

HRID 557568Notes

Reaction equation

HRID 557568 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15](=[O:18])[CH2:16]Br)=[CH:11][CH:12]=2)[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH3:19])[CH2:6][C:5]1([CH3:27])[CH3:26])(=[O:3])[CH3:2].[F:28][C:29]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32].C(N(CC)C(C)C)(C)C>O1CCOCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15]([CH2:16][NH:32][CH2:31][C:30]3[CH:33]=[CH:34][C:35]([F:37])=[CH:36][C:29]=3[F:28])=[O:18])=[CH:11][CH:12]=2)[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH3:19])[CH2:6][C:5]1([CH3:27])[CH3:26])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27332442,4-DifluorobenzylamineHCID 179628791-Acetyl-6-(bromoacetyl)amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

Product 1

HCID 179629131-Acetyl-6-([2,4-difluorobenzylamino]methylcarbonyl)amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1-acetyl-6-(bromoacetyl)amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (10 mg), 2,4-difluorobenzylamine (6.0 mg) and N,N-diisopropylethylamine (10 μl) in dioxane (2 ml) was stirred at 40° C. for 18 h. The reaction mixture was concentrated in vacuo. The residue was chromatographed on silicagel in dichloromethane/methanol=1/095/5 (v/v) as eluent.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was chromatographed on silicagel in dichloromethane/methanol=1/095/5 (v/v) as eluent

Sources & evidence

ORD record
ord-a182c595631942eb81b213c6bc2b4507
Source dataset
uspto-grants-2011_11
Patent number
US08058441B2

Reaction notes

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