Diisopropylethylamine → 1-Acetyl-6-(3-bromo-2,6-dimethoxybenzoyl)amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

HRID 557549

반응식

HRID 557549 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH2:6][C:5]1([CH3:23])[CH3:22])(=[O:3])[CH3:2].[Br:24][C:25]1[C:26]([O:36][CH3:37])=[C:27]([C:31]([O:34][CH3:35])=[CH:32][CH:33]=1)[C:28](O)=[O:29].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>ClCCl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:28](=[O:29])[C:27]3[C:31]([O:34][CH3:35])=[CH:32][CH:33]=[C:25]([Br:24])[C:26]=3[O:36][CH3:37])=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH2:6][C:5]1([CH3:23])[CH3:22])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27747443-Bromo-2,6-dimethoxybenzoic acidHCID 28370841-(6-amino-2,2,4-trimethyl-4-phenyl-3,4-dihydroquinolin-1(2H)-yl)ethanoneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 179628961-Acetyl-6-(3-bromo-2,6-dimethoxybenzoyl)amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 1-acetyl-6-amino-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (25 mg), 3-bromo-2,6-dimethoxybenzoic acid (23 mg), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (68 mg) and N,N-diisopropylethylamine (32 μl) in dichloromethane (4 ml) was stirred for 18 h. The reaction mixture was concentrated in vacuo, the residue was dissolved in ethyl acetate and washed with 0.5 M HCl, water, 5% aq. NaHCO3, water and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silicagel in heptane/ethyl acetate=1/0=>0/1 (v/v) as eluent.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 0.5 M HCl, water, 5% aq. NaHCO3, water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silicagel in heptane/ethyl acetate=1/0=>0/1 (v/v) as eluent

출처 및 근거

ORD 기록
ord-609633e1acf347c0a59a78e3f0efca2e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058441B2

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