Ethanol → HCID 67288893, compound

HRID 1626472Notes

Reaction equation

HRID 1626472 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:34])[NH:20][C:21]3[CH:22]=[N:23][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=4)=[N:25][CH:26]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([O:37]CC)=[O:36].[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:14]=[CH:15][C:16]([C:19](=[O:34])[NH:20][C:21]3[CH:26]=[N:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=4)=[N:23][CH:22]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([OH:37])=[O:36]

Participants

7

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67287686HCID 67287686, compound

Product 1

HCID 67288893HCID 67288893, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 6-chloro-7-(4-(2-(3-chlorophenyl)pyrimidin-5-ylcarbamoyl)phenoxy)chroman-4-carboxylate (45 mg, 0.080 mmol) was diluted with THF (1 mL) followed by the addition of NaOH (399 μl, 0.40 mmol) and ethanol (500 uL). 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 (15 mg, 0.028 mmol, 35% yield) MS (ESI)=536.1 (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-44a6c5cff11c43e29b909eb6ad19d4d8
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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