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

HRID 405186

Reaction equation

HRID 405186 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cf1fef51d5b3431c96f6ea6a8cd4ae49
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Linked notes

Loading…