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

HRID 405186

反応式

HRID 405186 の反応式
[CH:1]([C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([C:13]([F:16])([F:15])[F:14])=[CH:5][C:4]=1[C:17]1[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=1)=O.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=2)=[CH:36][CH:35]=1.CCO.[BH4-].[Na+]>CS(C)=O.C(Cl)Cl.O>[Cl:33][C:34]1[CH:35]=[CH:36][C:37]([C:40]2[CH:45]=[CH:44][C:43]([NH:46][CH2:1][C:3]3[C:8]([C:9]([F:12])([F:10])[F:11])=[CH:7][C:6]([C:13]([F:14])([F:15])[F:16])=[CH:5][C:4]=3[C:17]3[CH:18]=[CH:19][C:20]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[N:21][CH:22]=3)=[CH:42][CH:41]=2)=[CH:38][CH:39]=1

参加物

8

反応物 4

HCID 702Ethanol2 回HCID 86754-Amino-4'-chlorodiphenylHCID 4311764Sodium borohydride2 回HCID 86674260Ethyl 3-(5-(2-formyl-3,5-bis(trifluoromethyl)phenyl)picolinamido)propanoate

生成物 1

HCID 86674261Ethyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-3,5-bis(trifluoromethyl)phenyl)picolinamido)propanoate

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

Ethyl 3-(5-(2-formyl-3,5-bis(trifluoromethyl)phenyl)picolinamido)propanoate (76 mg, 0.16 mmol) and 4′-chloro-[1,1′-biphenyl]-4-amine (40 mg, 0.20 mmol) in DMSO (0.16 mL) was stirred at 100° C. After 30 min EtOH (0.16 mL) was added and the resulting homogeneous solution was stirred at 100° C. After 1 h the resulting homogeneous solution was cooled to room temperature, and NaBH4 (20 mg, 0.53 mmol), EtOH (1 mL), and DMSO (0.5 mL) were added and the resulting mixture was stirred. After 30 min, additional NaBH4 (20 mg, 0.53 mmol) was added and the resulting homogeneous solution was stirred. After 20 min the resulting mixture was diluted with DCM (5 mL) and 1 M NaH2PO4 (4 mL) was carefully added. Water was added and the aqueous phase was extracted with DCM. The combined organic layers were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

後処理

  1. temperatureAfter 1 h the resulting homogeneous solution was cooled to room temperature
  2. stirringthe resulting mixture was stirred
  3. stirringthe resulting homogeneous solution was stirred
  4. additionwas carefully added
  5. extractionthe aqueous phase was extracted with DCM
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified via column chromatography

出典と根拠

ORDレコード
ord-cf1fef51d5b3431c96f6ea6a8cd4ae49
出典データセット
uspto-grants-2014_06
特許番号
US08748624B2

関連ノート

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