Hydrochloric Acid → HCID 66697267, compound

HRID 2096816Notes

Reaction equation

HRID 2096816 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:40])[C:18]([C:24]3[CH:39]=[CH:38][C:27]4[N:28](CC=C)[C:29](=[O:34])[N:30](CC=C)[C:26]=4[CH:25]=3)([OH:23])[C:19]([F:22])([F:21])[F:20])=[C:13]([Cl:41])[CH:12]=2)=[CH:7][C:6]=1[F:42])=[O:4].Cl.[Li+].[OH-]>C(O)CC>[Cl:41][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[C:6]([F:42])[CH:7]=2)[CH:16]=[CH:15][C:14]=1[CH:17]([CH3:40])[C:18]([OH:23])([C:24]1[CH:39]=[CH:38][C:27]2[NH:28][C:29](=[O:34])[NH:30][C:26]=2[CH:25]=1)[C:19]([F:22])([F:20])[F:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66697362HCID 66697362, compound

Product 1

HCID 66697267HCID 66697267, compoundYield 24.9%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of RhCl3 trihydrate (2.5 mg) and 3′-chloro-4′-[2-(1,3-diallyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-3-fluoro-biphenyl-4-carboxylic acid methyl ester (57 mg) in n-PrOH (2 ml) was heated for 2 h to 100° C. in a sealed tube. 25% aqueous HCl (1 ml) was added and heating continued for 2 h at 100° C. The mixture was alkalized by addition of LiOH and stirred for 30 min at room temperature. Volatile solvents were evaporated and the residue dissolved in 1N aqueous NaOH (10 ml). The aqueous phase was washed with ether, acidified with 25% aqueous HCl and then extracted with EtOAc. The combined org. phases were dried over Na2SO4 and then concentrated to an oil. The residue was purified by prep. HPLC (C18-column, solvent gradient 20-98% CH3CN in 0.1% HCOOH[aq]) to give the title compound (12 mg) as a white solid. MS (m/e)=509.3 [M+H+].

Workup

  1. temperaturewas heated for 2 h to 100° C. in a sealed tube
  2. temperatureheating
  3. customVolatile solvents were evaporated
  4. dissolutionthe residue dissolved in 1N aqueous NaOH (10 ml)
  5. washThe aqueous phase was washed with ether
  6. extractionextracted with EtOAc
  7. dry with materialphases were dried over Na2SO4
  8. concentrationconcentrated to an oil
  9. customThe residue was purified by prep

Sources & evidence

ORD record
ord-9184df4029c14a8eb77fd9c212a482b9
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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