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 405194ノート

反応式

HRID 405194 の反応式
[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

参加物

8

反応物 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydride2 回HCID 600391884'-Chloro-2-methyl-[1,1'-biphenyl]-4-amineHCID 86674266Ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

生成物 1

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

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒HCID 11430Potassium Carbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f48091eecadf41bdbabbc4e8e1f46027
出典データセット
uspto-grants-2014_06
特許番号
US08748624B2

反応ノート

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