Ethanol → 6-Chloro-7-(4-(4-(4-(trifluoromethyl)phenyl)pyrimidin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid

HRID 1626469Notes

Reaction equation

HRID 1626469 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:37])[NH:20][C:21]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH:24]=[CH:23][N:22]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:38]([O:40]CC)=[O:39].[OH-].[Na+].C(O)C>C1COCC1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:37])[NH:20][C:21]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH:24]=[CH:23][N:22]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:38]([OH:40])=[O:39]

Participants

7

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67287776Ethyl 6-chloro-7-(4-(4-(4-(trifluoromethyl)phenyl)pyrimidin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate

Product 1

HCID 672878876-Chloro-7-(4-(4-(4-(trifluoromethyl)phenyl)pyrimidin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylic acidYield 10.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 6-chloro-7-(4-(4-(4-(trifluoromethyl)phenyl)pyrimidin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (50 mg, 0.084 mmol) was diluted with THF (1 mL) followed by the addition of NaOH (502 μL, 0.50 mmol) and ethanol (500 μL). After stirring for 2 hours, the reaction was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The residue was purified using a 0.5 mm preparative TLC plate eluting with 10% methanol/DCM to yield the desired compound (5 mg, 0.0088 mmol, 10% yield). MS (ESI)=570.1 (M+H)

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified
  6. washeluting with 10% methanol/DCM

Sources & evidence

ORD record
ord-105329faf1514ca984573c9aac433d05
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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