Potassium Carbonate → tert-Butyl 4-(2-ethynyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate

HRID 1772723

反応式

HRID 1772723 の反応式
[CH:1]([C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=3)[N:6]2[CH:30]=1)=O.[N+](=[C:33](P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CO>[C:1]([C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])=[CH:28][CH:29]=3)[N:6]2[CH:30]=1)#[CH:33]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 117733763tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoateHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

生成物 1

HCID 117732303tert-Butyl 4-(2-ethynyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of compound 81a (239 mg, 0.580 mmol) in anhydrous THF (8 mL) and anhydrous MeOH (3 mL), dimethyl (1-diazo-2-oxopropyl)phosphonate (164 mg, 0.850 mmol) in MeOH (2 mL) was added followed by potassium carbonate (252 mg, 1.82 mmol). The resulting yellow suspension was stirred at rt for 18 h. The mixture was filtered through a pad of diatomaceous earth. The filter cake was washed CH2Cl2. The combined filtrates were concentrated under reduced pressure. The residue was dissolved in DCM and washed with diluted NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on preparative TLC (EtOAc/CH2Cl2; 2:3, v/v) to afford compound 81b. Mass Spectrum (LCMS, ESI pos.): Calcd. for C23H25N4O3: 405.2 (M+H). found: 405.4.

後処理

  1. additionwas added
  2. filtrationThe mixture was filtered through a pad of diatomaceous earth
  3. washThe filter cake was washed CH2Cl2
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in DCM
  6. washwashed with diluted NaHCO3, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified on preparative TLC (EtOAc/CH2Cl2

出典と根拠

ORDレコード
ord-c3a536e52f4043cfb6fe22adb9298315
出典データセット
uspto-grants-2016_02
特許番号
US09249163B2

関連ノート

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