Hydrochloric Acid → 3-(5-(2-(((4'-Chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-6-(trifluoromethyl)phenyl)picolinamido)propanoic acid

HRID 405181Notes

Reaction equation

HRID 405181 reaction equation
[OH-].[Na+].C1COCC1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[C:24]=3[C:33]3[CH:34]=[CH:35][C:36]([C:39]([NH:41][CH2:42][CH2:43][C:44]([O:46]CC)=[O:45])=[O:40])=[N:37][CH:38]=3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.Cl>CO>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:32])[F:31])[C:24]=3[C:33]3[CH:34]=[CH:35][C:36]([C:39]([NH:41][CH2:42][CH2:43][C:44]([OH:46])=[O:45])=[O:40])=[N:37][CH:38]=3)=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71059902Ethyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-6-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 710599223-(5-(2-(((4'-Chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-6-(trifluoromethyl)phenyl)picolinamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1M aqueous solution of NaOH (0.30 mL, 0.30 mmol) was added to a THF (0.6 mL) and MeOH (0.3 mL) solution of ethyl 3-(5-(2-(((4′-chloro-[1,1′-biphenyl]-4-yl)amino)methyl)-6-(trifluoromethyl)phenyl)picolinamido)propanoate (57.5 mg, 0.10 mmol) and the resulting homogeneous mixture was stirred at room temperature. After 45 min the resulting mixture was acidified with 1M HCl (0.31 mL, 0.31 mmol) and then extracted with DCM. The combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-882dde1a17004ef6a80b781ce4d4ab2d
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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