Triethylamine → 4-Methyl-N-(5-methylisoxazol-4-yl)-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzamide

HRID 641977ノート

反応式

HRID 641977 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)[CH:18]=2)[N:13]=[CH:12]1.Cl.[NH2:30][C:31]1[CH:32]=[N:33][O:34][C:35]=1[CH3:36].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:30][C:31]2[CH:32]=[N:33][O:34][C:35]=2[CH3:36])=[O:7])=[CH:4][C:3]=1[N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)[CH:18]=2)[N:13]=[CH:12]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 130332035-Methyl-1,2-oxazol-4-amine hydrochlorideHCID 669188194-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoic acid

生成物 1

HCID 119970164-Methyl-N-(5-methylisoxazol-4-yl)-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzamide収率 32.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred slurry of 4-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3(4H)-yl]benzoic acid (0.38 g) in DMF (50 ml) was added 4-amino-5-methylisoxazole hydrochloride (0.27 g), HATU (0.68 g) and triethylamine (0.55 ml) and the reaction mixture stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with 1N NaOH and dried (magnesium sulphate). The residue was purified by column chromatography on a silica column using initially ethyl acetate and then a 4:1 mixture of ethyl acetate and methanol as eluent. There was thus obtained the title compound (150 mg); NMR Spectrum: (DMSOd6) 2.15 (s, 3H), 2.40 (s, 3H), 2.83 (m, 4H), 3.15 (s, 3H), 3.40 (m, 4H), 7.50 (d, 1H), 7.60 (d, 1H), 7.64 (m, 2H), 7.98 (s, 1H), 8.04 (d, 1H), 8.13 (s, 1H), 8.70 (s, 1H), 10.10 (s, 1H); Mass Spectrum: M+H+ 459.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with 1N NaOH
  3. dry with materialdried (magnesium sulphate)
  4. customThe residue was purified by column chromatography on a silica column
  5. additiona 4:1 mixture of ethyl acetate and methanol as eluent

出典と根拠

ORDレコード
ord-c0c7409d52bf42deaf8e94f9250805be
出典データセット
uspto-grants-2010_04
特許番号
US07696215B2

反応ノート

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