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

HRID 641982노트

반응식

HRID 641982 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b66f83daba6d4472b2b66ec864a7f6fb
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696215B2

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