1,1'-Carbonyldiimidazole → 4-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-6-oxa-4-azaspiro[2.4]heptane-5-one

HRID 1436379ノート

反応式

HRID 1436379 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH:13][C:14]3([CH2:17][OH:18])[CH2:16][CH2:15]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.[C:19](N1C=CN=C1)(N1C=CN=C1)=[O:20]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:13]3[C:19](=[O:20])[O:18][CH2:17][C:14]43[CH2:15][CH2:16]4)[S:11][CH:12]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86618582(1-{[4-(4-Bromophenyl)-1,3-thiazol-2-yl]amino}cyclopropyl)methanol

生成物 1

HCID 250273724-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-6-oxa-4-azaspiro[2.4]heptane-5-one収率 75%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
165 °C

実験手順

A mixture of (1-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}cyclopropyl)methanol (0.7598 g 2.34 mmol), prepared in previous step, and 15 mL of anhydrous acetonitrile were sonicated for 1 min and then stirred on a vortex stirrer for 2 min. To the resulting solution, carbonyldiimidazole (0.5683 g, 3.5 mmol) was added and the mixture again sonicated for 1 min and stirred on a vortex stirrer for 2 min. The resulting solution was then heated in an Emrys™ Optimizer microwave oven at 165° C. for 20 min. Upon cooling to room temperature crystals began to form. The crystals were collected by filtration and the filtrate was concentrated under reduced pressure. The residue was partitioned between methylene chloride and 2N HCl. The organic layer was separated, washed with water, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material obtained was combined with the crystalline material previously isolated to give the title compound (607.9 mg 75%) as a white solid, mp 201-202° C.; MS (ESI) m/z 351. HRMS: calcd for C14H11BrN2O2S+H+, 350.97973; found (ESI, [M+H]+), 350.9806.

後処理

  1. customwere sonicated for 1 min
  2. customthe mixture again sonicated for 1 min
  3. stirringstirred on a vortex stirrer for 2 min
  4. temperatureUpon cooling to room temperature crystals
  5. customto form
  6. filtrationThe crystals were collected by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was partitioned between methylene chloride and 2N HCl
  9. customThe organic layer was separated
  10. washwashed with water
  11. dry with materialdried over anhydrous MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe material obtained
  15. custompreviously isolated

出典と根拠

ORDレコード
ord-94918e542881438e9eb338635cf8b116
出典データセット
uspto-grants-2009_11
特許番号
US07618990B2

反応ノート

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