1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178521594、化合物

HRID 1672470

反応式

HRID 1672470 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 178521594HCID 178521594、化合物収率 35%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
45 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f8c505d937f4476b9115cfed19668f52
出典データセット
uspto-grants-2011_08
特許番号
US07998978B2

関連ノート

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