Potassium Carbonate → (S)-9-neopentyl-7-(2-(4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidin-1-yl)ethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one

HRID 132278

반응식

HRID 132278 반응식
O[CH2:2][CH2:3][C@H:4]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:15][C:7]2[C:8]3[CH:9]=[N:10][NH:11][C:12]=3[CH:13]=[CH:14][C:6]=2[CH2:5]1.S(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+].[NH:34]1[CH2:39][CH2:38][CH:37]([N:40]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[NH:42][C:41]2=[O:50])[CH2:36][CH2:35]1>ClCCl>[CH2:19]([N:16]1[C:17](=[O:18])[C@H:4]([CH2:3][CH2:2][N:34]2[CH2:35][CH2:36][CH:37]([N:40]3[CH2:49][C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[NH:42][C:41]3=[O:50])[CH2:38][CH2:39]2)[CH2:5][C:6]2[CH:14]=[CH:13][C:12]3[NH:11][N:10]=[CH:9][C:8]=3[C:7]=2[CH2:15]1)[C:20]([CH3:23])([CH3:22])[CH3:21]

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 24386Thionyl Chloride2회HCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 59731990(S)-7-(2-hydroxyethyl)-9-neopentyl-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one

생성물 1

HCID 59731988(S)-9-neopentyl-7-(2-(4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidin-1-yl)ethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one수율 25%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(S)-7-(2-hydroxyethyl)-9-neopentyl-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one (15 mg, 0.04 mmol) was dissolved in dichloromethane (1 mL). Thionyl chloride (100 μL) was added to the mixture. Reaction stirred at room temperature for 2 hours. Thionyl chloride (500 μL) was added to the mixture. Reaction stirred at room temperature for 2 hours and then was warmed to reflux for 2 hours. Reaction mixture was concentrated in vacuo. Residue was dissolved in acetonitrile (1 mL). Potassium carbonate (25 mg, 0.18 mmol) was added to the mixture followed by 3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (16 mg, 0.07 mmol). Reaction was heated at reflux for 2 hours. Preparatory HPLC purification afforded the title compound as white solid in 25% yield. High resolution MS m/e (M+H)+=529.3282.

후처리

  1. customReaction
  2. customReaction
  3. stirringstirred at room temperature for 2 hours
  4. temperaturewas warmed
  5. temperatureto reflux for 2 hours
  6. customReaction mixture
  7. concentrationwas concentrated in vacuo
  8. dissolutionResidue was dissolved in acetonitrile (1 mL)
  9. customReaction
  10. temperaturewas heated
  11. temperatureat reflux for 2 hours
  12. customPreparatory HPLC purification

출처 및 근거

ORD 기록
ord-7912f09f8a5b4fd6ae4c1f7447ac0f1a
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384930B2

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