Acetic Acid → Ethyl 3-(5-(3-chloro-2-(((4'-chloro-2-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405194노트

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HRID 405194 반응식
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:15][C:16]1[C:17]([CH:42]=O)=[C:18]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:33])=[N:30][CH:31]=2)[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:56]=[CH:55][C:54]([NH2:57])=[CH:53][C:52]=2[CH3:58])=[CH:47][CH:46]=1.CC(O)=O>CCOC(C)=O.C([O-])([O-])=O.[K+].[K+].ClCCCl>[Cl:15][C:16]1[C:17]([CH2:42][NH:57][C:54]2[CH:55]=[CH:56][C:51]([C:48]3[CH:49]=[CH:50][C:45]([Cl:44])=[CH:46][CH:47]=3)=[C:52]([CH3:58])[CH:53]=2)=[C:18]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:33])=[N:30][CH:31]=2)[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydride2회HCID 600391884'-Chloro-2-methyl-[1,1'-biphenyl]-4-amineHCID 86674266Ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

생성물 1

HCID 71060161Ethyl 3-(5-(3-chloro-2-(((4'-chloro-2-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 8857Ethyl Acetate용매HCID 11430Potassium Carbonate용매

실험 절차

Solid NaBH(OAc)3 (2.6 g, 12.1 mmol) was added to a DCE solution (16 mL) of ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate (2.6 g, 6.1 mmol) and 4′-chloro-2-methyl-[1,1′-biphenyl]-4-amine (1.6 g, 7.3 mmol), and AcOH (1.4 mL, 1.2 mmol) and the resulting mixture was stirred at room temperature. After 2 h additional NaBH(OAc)3 (2.6 g, 12.1 mmol) was added. After 4 h the resulting mixture was diluted with EtOAc and 2M aqueous K2CO3 and the layers were separated. The aqueous phase was added was extracted with EtOAc and the combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

후처리

  1. customthe layers were separated
  2. additionThe aqueous phase was added
  3. extractionwas extracted with EtOAc
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified via column chromatography

출처 및 근거

ORD 기록
ord-f48091eecadf41bdbabbc4e8e1f46027
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748624B2

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