1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178521594, 화합물

HRID 1672470노트

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HRID 1672470 반응식
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]=[CH:7]2.[NH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]1)[N:8]=[CH:7]2

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 457900618-Bromo-2-chloroquinazolineHCID 178511715HCID 178511715, 화합물

생성물 1

HCID 178521594HCID 178521594, 화합물수율 35%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
45 °C

실험 절차

To a solution of 8-bromo-2-chloroquinazoline (7.3 g, 30 mmol) in acetonitrile (150 mL) was added trans-4-aminocyclohexanol (6.9 g, 60 mmol) to form a suspension. DBU (9.1 g, 60 mmol) was added. The reaction mixture was stirred at 45° C. overnight. A light yellow suspension was formed. The solvent was removed under reduced pressure, and the residue was taken into DCM (100 mL) and washed with water (100 mL). The organic layer was dried over Na2SO4 and purified by chromatography (eluting with DCM) to give the title compound as a light yellow solid (3.36 g, 35%). 1HNMR (DMSO-d6, 400 MHz): δ 9.10 (s, 1H), 8.02 (dd, J=1.2, 7.6 Hz, 1H), 7.81 (dd, J=1.2, 7.6 Hz, 1H), 7.62-7.60 (m, 1H), 7.12 (dd, J=7.6, 7.6 Hz, 1H), 4.62-4.60 (m, 1H), 3.85-3.82 (m, 1H), 2.05-2.02 (m, 2H), 1.89-1.86 (m, 2H), 1.36-1.26 (m, 4H).

후처리

  1. customto form a suspension
  2. customA light yellow suspension was formed
  3. customThe solvent was removed under reduced pressure
  4. washwashed with water (100 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. custompurified by chromatography (eluting with DCM)

출처 및 근거

ORD 기록
ord-f8c505d937f4476b9115cfed19668f52
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998978B2

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