Trifluoroacetic acid → HCID 54755866、化合物

HRID 2191596ノート

反応式

HRID 2191596 の反応式
[CH:1]1([NH:7][C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:17]=3)[N:12](COCC[Si](C)(C)C)[CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([NH:7][C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([O:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 67002498HCID 67002498、化合物

生成物 1

HCID 54755866HCID 54755866、化合物収率 22%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyclohexylamide from Step 3 in dichloromethane (0.7 mL) was added trifluoroacetic acid (0.7 mL). The reaction mixture was stirred at room temperature overnight then concentrated. The residue was stirred with THF (1 mL), water (0.5 mL), and Et3N (0.5 mL) for 2 h then concentrated. The residue was partitioned between ethyl acetate and water and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by SiO2 column chromatography (0% to 80% EtOAc/hexanes) then triturated with Et2O to provide 0.022 g (22%, 2 steps) of 2-phenoxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyclohexylamide as a white solid. MS: (M+H)+=337; mp=255.0-257.0.

後処理

  1. concentrationthen concentrated
  2. stirringThe residue was stirred with THF (1 mL), water (0.5 mL), and Et3N (0.5 mL) for 2 h
  3. concentrationthen concentrated
  4. customThe residue was partitioned between ethyl acetate and water
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by SiO2 column chromatography (0% to 80% EtOAc/hexanes)
  9. customthen triturated with Et2O

出典と根拠

ORDレコード
ord-3f138dabf04c4b59b299f6f20065724c
出典データセット
uspto-grants-2012_12
特許番号
US08329699B2

反応ノート

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