Phosphorus oxychloride → N-Isoxazol-3-Yl-4-Methyl-3-[6-(4-Methylpiperazin-1-Yl)-4-Oxo-Quinazolin-3-Yl]benzamide

HRID 641945노트

반응식

HRID 641945 반응식
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=1[N:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([N:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)[CH:23]=2)[N:18]=[CH:17]1.[NH2:34][C:35]1[CH:39]=[CH:38][O:37][N:36]=1>N1C=CC=CC=1>[O:37]1[CH:38]=[CH:39][C:35]([NH:34][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][C:7]([CH3:6])=[C:8]([N:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([N:27]5[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]5)[CH:23]=4)[N:18]=[CH:17]3)[CH:9]=2)=[N:36]1

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 18102163-IsoxazolamineHCID 669188194-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoic acid

생성물 1

HCID 11554076N-Isoxazol-3-Yl-4-Methyl-3-[6-(4-Methylpiperazin-1-Yl)-4-Oxo-Quinazolin-3-Yl]benzamide

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Phosphorus oxychloride (0.11 ml) was added to a mixture of 4-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoic acid (0.30 g), 3-aminoisoxazole (0.12 ml) and pyridine (5 ml) and the resultant suspension was heated to 120° C. for 5 minutes in a microwave (Personal Chemistry Emrys Optimizer with 300 W magnetron). The mixture was evaporated. The residue was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic phase was dried (magnesium sulphate), evaporated and the residue purified by column chromatography on a silica column using initially methylene chloride and then a 9:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.14 g); NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 2.24 (s, 3H), 2.49 (m, 4H), 3.29 (m, 4H), 7.06 (d, 1H), 7.50 (d, 1H), 7.63 (m, 3H), 8.09 (m, 2H), 8.13 (s, 1H), 8.85 (d, 1H), 11.46 (s, 1H); Mass Spectrum: M+H+ 445.

후처리

  1. customThe mixture was evaporated
  2. customThe residue was partitioned between ethyl acetate and saturated NaHCO3 solution
  3. dry with materialThe organic phase was dried (magnesium sulphate)
  4. customevaporated
  5. customthe residue purified by column chromatography on a silica column
  6. additiona 9:1 mixture of methylene chloride and methanol as eluent

출처 및 근거

ORD 기록
ord-60e44bdf2192407ca0e9a2250f964cf4
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696215B2

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