(4-[4-(2-Oxo-1,2-dihydro-quinolin-3-yl)-thiazol-2-yl]-phenyl)-carbamic acid tert-butyl ester → 3-[2-(4-Amino-phenyl)-thiazol-4-yl]-1H-quinolin-2-one

HRID 2416202노트

반응식

HRID 2416202 반응식
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[C:20](=[O:29])[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:18]=2)=[CH:10][CH:9]=1)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[C:20](=[O:29])[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:18]=2)=[CH:10][CH:9]=1

참가 물질

4

반응물 1

HCID 58810140(4-[4-(2-Oxo-1,2-dihydro-quinolin-3-yl)-thiazol-2-yl]-phenyl)-carbamic acid tert-butyl ester

생성물 1

HCID 101497433-[2-(4-Amino-phenyl)-thiazol-4-yl]-1H-quinolin-2-one

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of {4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-thiazol-2-yl]-phenyl}-carbamic acid tert-butyl ester (Example 97, 70 mg, 0.17 mmol) in 0.8 mL of CH2Cl2 and 0.8 mL of TFA was stirred at RT for 1 h. Solvents were removed under vacuum and the residue was azeotroped twice with toluene. To the flask, 4.0 mL of aqueous HCl (1 M) was added and solids formed. The solvent was removed again and the solid was azeotroped with toluene twice. The solid was dried under vacuum overnight to afford the title compound as a light yellow solid. MS m/z: 320.2 (M+1). Anal. Calc'd for C18H13N3OS.0.8H2O.1.6HBr: C, 55.13; H, 4.16; N, 10.72; O, 7.34; S, 8.18. Found: C, 55.24; H, 4.15; N, 10.66; O, 7.45; S, 8.21.

후처리

  1. customSolvents were removed under vacuum
  2. customthe residue was azeotroped twice with toluene
  3. additionTo the flask, 4.0 mL of aqueous HCl (1 M) was added
  4. customsolids formed
  5. customThe solvent was removed again
  6. customthe solid was azeotroped with toluene twice
  7. customThe solid was dried under vacuum overnight

출처 및 근거

ORD 기록
ord-dbd737f8962f4d6baa76ba3ef44e7b8b
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06822097B1

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