Hydrochloric Acid → HCID 73297228, compound

HRID 530405Notes

Reaction equation

HRID 530405 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27]C)=[O:26])[CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.[OH-].[Na+].Cl>CO.[Cl-].[Na+].O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([OH:27])=[O:26])[CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90041495HCID 90041495, compound

Product 1

HCID 73297228HCID 73297228, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of methyl 3′-methyl-5′-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-3-carboxylate (550 mg, 1.420 mmol) and aqueous sodium hydroxide (1 M, 1.63 mL, 1.63 mmol) in methanol (9 mL) was heated to 110° C. for 10 minutes in a microwave reactor. The reaction mixture was then diluted with aqueous hydrochloric acid (2 M, 0.89 mL, 1.78 mmol), brine (20 mL), and ethyl acetate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (15 mL). The combined organic layers were washed with brine (20 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 3′-methyl-5′-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-3-carboxylic acid. MS ESI calc'd. for C19H15F3N3O2 [M+H]+ 374, found 374.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (15 mL)
  3. washThe combined organic layers were washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1cd0ede9a3e641a5ba7ea8512d62b0d6
Source dataset
uspto-grants-2016_05
Patent number
US09353066B2

Reaction notes

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