Sodium Hydroxide → 1-Amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522444ノート

反応式

HRID 1522444 の反応式
[NH2:1][N:2]1[C:6]2[N:7]=[C:8]([CH:16]3[CH2:18][CH2:17]3)[CH:9]=[C:10]([C:11]([O:13]CC)=[O:12])[C:5]=2[CH:4]=[N:3]1.[OH-].[Na+]>C(O)C>[NH2:1][N:2]1[C:6]2[N:7]=[C:8]([CH:16]3[CH2:17][CH2:18]3)[CH:9]=[C:10]([C:11]([OH:13])=[O:12])[C:5]=2[CH:4]=[N:3]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 67124432Ethyl 1-amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

生成物 1

HCID 671242951-Amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl 1-amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (100 mg, 0.406 mmol) in ethanol (10 mL) was added sodium hydroxide (1 ml, 0.406 mmol), and the mixture stirred at room temperature for 2 h. The solvent was removed in vacuo, and the residue diluted with EtOAc (30 mL) and water (20 mL). The reaction mixture was acidified to pH 3 with citric acid. The phases were separated and the aq. phase extracted with EtOAc (4×20 mL). The combined organic layers were washed with water, dried over MgSO4, filtered, and concentrated in vacuo. The final product was collected as 0.075 g (84%). LCMS E-S (M+H)=219.5. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.00-1.13 (m, 4 H), 2.27-2.45 (m, 1 H), 6.36 (s, 2 H), 7.60 (s, 1 H), 8.06 (s, 1 H), 13.81 (br. s., 1 H).

後処理

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted with EtOAc (30 mL) and water (20 mL)
  3. customThe phases were separated
  4. extractionthe aq. phase extracted with EtOAc (4×20 mL)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe final product was collected as 0.075 g (84%)

出典と根拠

ORDレコード
ord-428693c697ff445d86f9822570b36cab
出典データセット
uspto-grants-2015_07
特許番号
US09073924B2

反応ノート

読み込み中…