Trifluoroacetic acid → 2-(4-(4-Aminopiperidin-1-yl)quinazolin-2-yl)phenol

HRID 2062293노트

반응식

HRID 2062293 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24]C(=O)OC(C)(C)C)[CH2:20][CH2:19]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][CH:21]1[CH2:22][CH2:23][N:18]([C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[N:17]=2)[CH2:19][CH2:20]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 136121521Tert-butyl 1-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperidin-4-ylcarbamate

생성물 1

HCID 1361214062-(4-(4-Aminopiperidin-1-yl)quinazolin-2-yl)phenol수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 1-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperidin-4-ylcarbamate (3.27 g, 8.09 mmol) in CH2Cl2 (75 mL) was added TFA (50 mL). The reaction was complete after 45 minutes After evaporating the solvents in vacuo, the crude material was diluted with CH2Cl2 and neutralized by adding a 1 N aqueous NaOH solution. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×15 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated to afford 2-(4-(4-aminopiperidin-1-yl)quinazolin-2-yl)phenol as a solid (2.09 g, 84%). LC/MS: m/z 321.3 (M+H)+ at 1.28 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

후처리

  1. customAfter evaporating the solvents in vacuo
  2. additionthe crude material was diluted with CH2Cl2
  3. additionby adding a 1 N aqueous NaOH solution
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with CH2Cl2 (2×15 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-293e93075d1544199fcdda4f52df723e
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283354B2

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