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Hydrochloric Acid → 4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine

HRID 241105
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HRID 241105 반응식
[CH3:1][C:2]1([CH3:41])[CH2:11][CH2:10][C:9]2[N:8]=[CH:7][N:6]=[C:5]([N:12]3[CH2:18][C:17]4[CH:19]=[C:20]([C:23]5[CH:24]=[C:25]6[N:31](COCC[Si](C)(C)C)[C:30]([CH3:40])=[N:29][C:26]6=[N:27][CH:28]=5)[CH:21]=[CH:22][C:16]=4[O:15][CH2:14][CH2:13]3)[C:4]=2[CH2:3]1.Cl>CO>[CH3:1][C:2]1([CH3:41])[CH2:11][CH2:10][C:9]2[N:8]=[CH:7][N:6]=[C:5]([N:12]3[CH2:18][C:17]4[CH:19]=[C:20]([C:23]5[CH:24]=[C:25]6[NH:31][C:30]([CH3:40])=[N:29][C:26]6=[N:27][CH:28]=5)[CH:21]=[CH:22][C:16]=4[O:15][CH2:14][CH2:13]3)[C:4]=2[CH2:3]1
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참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 668205234-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-[2-methyl-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazo[4,5-b]pyridin-6-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepine

생성물 1

HCID 595866604-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine수율 67%

시약·촉매·용매 1

HCID 887Methanol
용매

실험 절차

A solution of 4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-[2-methyl-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazo[4,5-b]pyridin-6-yl]-2,3,4,5-tetrahydro-1,4-benzoxazepine (0.54 g, 0.95 mmol) in a mixture of methanol (30 mL) and concentrated hydrochloric acid (1 mL) was stirred at reflux for 16 hours. On cooling to room temperature the solution was concentrated and the pH was adjusted to ˜9 by the addition of 50% aqueous sodium hydroxide and diluted with ethyl acetate (100 mL). The organic layer was washed with 2M aqueous sodium hydroxide (20 mL) and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The precipitating white solid was collected by filtration and washed with hexane to provide 4-(6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-yl)-7-(2-methyl-1H-imidazo[4,5-b]pyridin-6-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine (0.28 g, 67%). 1H NMR (400 MHz, d6-DMSO): 8.53 (d, 1H), 8.38 (s, 1H), 8.03 (d, 1H), 7.70 (d, 1H), 7.54 (dd, 1H), 7.05 (d, 1H), 4.63 (s, 2H), 4.33 (m, 2H), 3.85 (m, 2H), 2.72 (m, 2H), 2.58 (s, 3H), 2.47 (s, 2H), 1.60 (m, 2H), 0.86 (s, 6H); MS (EI) for C26H28N6O: 441 (MH+).

후처리

  1. temperatureat reflux for 16 hours
  2. concentrationwas concentrated
  3. additionthe pH was adjusted to ˜9 by the addition of 50% aqueous sodium hydroxide
  4. additiondiluted with ethyl acetate (100 mL)
  5. washThe organic layer was washed with 2M aqueous sodium hydroxide (20 mL) and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationThe precipitating white solid was collected by filtration
  10. washwashed with hexane

출처 및 근거

ORD 기록
ord-6acb8a1effa5414896e5f974bd0db541
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08648066B2

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