Water → methyl 3-[6-[4-(cyclopropylmethyl)piperazin-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate

HRID 641982ノート

反応式

HRID 641982 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:19]=2)[N:14]=[CH:13]1.[C:29]1(=O)[CH2:32][CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:32]1([CH2:29][N:26]2[CH2:27][CH2:28][N:23]([C:18]3[CH:19]=[C:20]4[C:15](=[CH:16][CH:17]=3)[N:14]=[CH:13][N:12]([C:3]3[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=3[CH3:1])[C:6]([O:8][CH3:9])=[O:7])[C:21]4=[O:22])[CH2:24][CH2:25]2)[CH2:30][CH2:31]1

参加物

7

反応物 4

HCID 962WaterHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 68604387methyl 4-methyl-3-(4-oxo-6-piperazin-1-ylquinazolin-3(4H)-yl)benzoate

生成物 1

HCID 68603182methyl 3-[6-[4-(cyclopropylmethyl)piperazin-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 4-methyl-3-(4-oxo-6-piperazin-1-ylquinazolin-3(4H)-yl)benzoate (0.5 g) and cyclobutanone (0.20 ml) in THF (42.5 ml) was added titanium (IV) isopropoxide (0.75 ml) and the solution stirred at room temperature for 30 minutes. Sodium triacetoxyborohydride (0.83 g) was added and the reaction stirred at room temperature for 18 hours. Water was added and the resultant solid removed by filtration. The aqueous filtrate was washed with ethyl acetate. The organic layer was washed 1N NaOH (×2), water, brine, dried (magnesium sulphate) and to yield methyl 3-[6-[4-(cyclopropylmethyl)piperazin-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate as a yellow foam (0.45 g); NMR Spectrum: (DMSOd6) 1.66 (m, 2H), 1.84 (m, 2H), 2.00 m, 2H), 2.16 (s, 3H), 2.42 (m, 4H), 2.75 (m, 1H), 3.27 (m, 4H), 3.87 (s, 3H), 7.48 (s, 1H), 7.62 (m, 3H), 7.97 (s, 1H), 8.02 (d, 1H), 8.09 (s, 1H); Mass Spectrum: M+H+ 433.

後処理

  1. stirringthe reaction stirred at room temperature for 18 hours
  2. customthe resultant solid removed by filtration
  3. washThe aqueous filtrate was washed with ethyl acetate
  4. washThe organic layer was washed 1N NaOH (×2), water, brine
  5. dry with materialdried (magnesium sulphate)

出典と根拠

ORDレコード
ord-b66f83daba6d4472b2b66ec864a7f6fb
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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