Trifluoroacetic acid → HCID 54755866, 화합물

HRID 2191596노트

반응식

HRID 2191596 반응식
[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

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67002498HCID 67002498, 화합물

생성물 1

HCID 54755866HCID 54755866, 화합물수율 22%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3f138dabf04c4b59b299f6f20065724c
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329699B2

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