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Hydrochloric Acid → Ethyl 3-[2-fluoro-4-({4-[(propyl{4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzyl}oxy)phenyl]propanoate

HRID 732188
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HRID 732188 반응식
[CH2:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:9]=1)[CH2:2][CH3:3].[H-].[Na+].Cl[CH2:23][C:24]1[CH:45]=[CH:44][C:27]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:32]([F:43])[CH:31]=2)=[CH:26][CH:25]=1.Cl>CN(C)C=O>[F:43][C:32]1[CH:31]=[C:30]([O:29][CH2:28][C:27]2[CH:44]=[CH:45][C:24]([CH2:23][N:4]([CH2:1][CH2:2][CH3:3])[C:5]3[S:6][CH:7]=[C:8]([C:10]4[CH:11]=[CH:12][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:15]=4)[N:9]=3)=[CH:25][CH:26]=2)[CH:35]=[CH:34][C:33]=1[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 23082955N-Propyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amineHCID 23143241Ethyl 3-(4-([4-(chloromethyl)benzyl]oxy}-2-fluorophenyl)propanoate

생성물 1

HCID 23143337Ethyl 3-[2-fluoro-4-({4-[(propyl{4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzyl}oxy)phenyl]propanoate

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-propyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole-2-amine (700 mg, 2.44 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (100 mg, in oil, 2.5 mmol) at room temperature and the mixture was stirred at room temperature for 1 hr. Ethyl 3-(4-{[4-(chloromethyl)benzyl]oxy}-2-fluorophenyl)propanoate (700 mg, 2.0 mmol) was added and the mixture was further stirred at room temperature for 2 hr. The reaction mixture was poured into 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was concentrated and the residue was purified by preparative HPLC. The obtained fraction was concentrated, neutralized with 10% aqueous sodium hydrogencarbonate solution, and extracted with ethyl acetate. The ethyl acetate layer was filtered with a Presep Dehydration tube (Wako Pure Chemical Industries, Ltd.) and concentrated to give the title compound as a yellow oil.

후처리

  1. stirringthe mixture was further stirred at room temperature for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by preparative HPLC
  5. concentrationThe obtained fraction was concentrated
  6. extractionextracted with ethyl acetate
  7. filtrationThe ethyl acetate layer was filtered with a Presep Dehydration tube (Wako Pure Chemical Industries, Ltd.)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-393ba54bbc1a4255b272aa1a8fa4dddd
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07585880B2

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