Trifluoroacetic acid → tert-butyl 5-((5-chloro-2-((1-(cyclopropylmethyl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 1478054ノート

反応式

HRID 1478054 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.[CH:25]1([CH2:28][N:29]2[CH:33]=[C:32]([NH2:34])[CH:31]=[N:30]2)[CH2:27][CH2:26]1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[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:34][C:32]2[CH:31]=[N:30][N:29]([CH2:28][CH:25]3[CH2:27][CH2:26]3)[CH:33]=2)=[N:3][CH:4]=1

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 435603721-(cyclopropylmethyl)-1H-pyrazol-4-amineHCID 118389983tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

生成物 1

HCID 118390017tert-butyl 5-((5-chloro-2-((1-(cyclopropylmethyl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate収率 271.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of tert-butyl 5-[(2,5-dichloropyrimidin-4-yl)amino]-hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (1.10 g, 2.95 mmol) and 1-(cyclopropylmethyl)pyrazol-4-amine (38.5 mg, 0.28 mmol) in dioxane (10 mL) was added 2,2,2-trifluoroacetic acid (61.8 mg, 0.54 mmol). The reaction mixture was stirred at 100° C. overnight, then adjusted to pH=10 with a saturated Na2CO3 solution, and extracted with EtOAc (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 (EtOAc/PE (v/v)=1/2) to give the title compound as a pale yellow solid (0.36 g, 26%).

後処理

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

出典と根拠

ORDレコード
ord-1f2793e397904b85890e60d1dc2da834
出典データセット
uspto-grants-2016_08
特許番号
US09403801B2

反応ノート

読み込み中…