Hydrochloric Acid → HCID 118389991、化合物

HRID 1478050ノート

反応式

HRID 1478050 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)[C:5]([Cl:24])=[CH:4][N:3]=1.[NH2:25][C:26]1[CH:27]=[N:28][N:29]([CH2:31][CH2:32][OH:33])[CH:30]=1.Cl>CC(O)C>[Cl:24][C:5]1[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)=[N:7][C:2]([NH:25][C:26]2[CH:27]=[N:28][N:29]([CH2:31][CH2:32][OH:33])[CH:30]=2)=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 284922672-(4-Amino-1H-pyrazol-1-yl)ethanolHCID 118389983tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

生成物 1

HCID 118389991HCID 118389991、化合物収率 63.4%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
140 °C

実験手順

To a suspension of tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (633.5 mg, 1.70 mmol) and 2-(4-amino-1H-pyrazol-1-yl)ethanol (249.1 mg, 1.99 mmol) in i-PrOH (8 mL) was added a solution of HCl in EtOAC ((1 mL, 4 mmol)). The reaction mixture was stirred at 140° C. under microwave radiation for 1 h and concentrated in vacuo. The residue was dissolved in water (30 mL) and adjusted to pH=10 with a saturated Na2CO3 aqueous solution, then extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/30) to give the title compound as a yellow solid (0.50 g, 63%).

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. extractionextracted with DCM (100 mL×3)
  4. washThe combined organic phases were washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/30)

出典と根拠

ORDレコード
ord-ea78df19d8bd49e8a2d111a5d1fce791
出典データセット
uspto-grants-2016_08
特許番号
US09403801B2

反応ノート

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