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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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Reaktionsgleichung von HRID 241105
[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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4

Edukt 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

Produkt 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-benzoxazepineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6acb8a1effa5414896e5f974bd0db541
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08648066B2

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