Water → HCID 86690321、化合物

HRID 1428671ノート

反応式

HRID 1428671 の反応式
[NH2:1][C:2]1[C:3]([C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:7]=1.CC(C)([O-])C.[K+].O>C(O)(C)(C)C>[C:18]1([CH3:21])[CH:19]=[CH:20][C:15]([C:5]2[N:4]=[C:3]3[CH:22]=[C:23]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[NH:1][C:2]3=[N:7][C:6]=2[C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86690320HCID 86690320、化合物

生成物 1

HCID 86690321HCID 86690321、化合物

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

7-(3-Amino-5,6-di-p-tolylpyrazin-2-yl)hept-6-ynoic acid (step 1) (137 mg, 0.343 mmol) in tert-BuOH (3 ml) was treated with potassium tert-butoxide (154 mg, 1.372 mmol) and stirred at reflux for 3 hours. The mixture was added to water (50 ml) and extracted with DCM (×3). The organic solvent was removed under reduced pressure and the crude material was dissolved in EtOH (minimal) and excess of water was added. The resulting suspension was sonicated and filtered, rinsing the filter cake with water (×3). Purification of crude product by chromatograpy on silica eluting with 0-1% MeOH in DCM afforded the titled compound; LC-MS Rt 1.10 mins MS m/z 400.2 [M+H]+; Method 2 minLC_v003

後処理

  1. temperatureat reflux for 3 hours
  2. extractionextracted with DCM (×3)
  3. customThe organic solvent was removed under reduced pressure
  4. dissolutionthe crude material was dissolved in EtOH (minimal) and excess of water
  5. additionwas added
  6. customThe resulting suspension was sonicated
  7. filtrationfiltered
  8. washrinsing the filter cake with water (×3)
  9. customPurification of crude product by chromatograpy on silica eluting with 0-1% MeOH in DCM

出典と根拠

ORDレコード
ord-f17182ce5134437eb4ea560ccef60a86
出典データセット
uspto-grants-2015_01
特許番号
US08937069B2

反応ノート

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