Hydrochloric Acid → HCID 71144601, compound

HRID 1622573Notes

Reaction equation

HRID 1622573 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:13]([C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][N:30]=2)[NH:14][C:15](=[O:28])[NH:16][C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[Li+].[OH-].Cl>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([C@@H:13]([C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][N:30]=2)[NH:14][C:15](=[O:28])[NH:16][C:17]2[CH:27]=[CH:26][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:10])([F:11])[F:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71164809HCID 71164809, compound

Product 1

HCID 71144601HCID 71144601, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-ethyl 4-(3-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)ureido)benzoate (109 mg, 0.220 mmol) in THF (3 mL) and MeOH (1 mL) was added 1 M aqueous LiOH (4 mL, 4.00 mmol). The resulting mixture was then stirred at rt. After stirring for 24 h, the reaction was acidified with 1 N HCl to ˜pH 7. The aqueous solution was extracted with DCM (3×10 mL). The combined DCM layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound as an off-white solid. 1H-NMR (300 MHz, MeOH-d4): δ ppm 8.48 (d, J=4.7 Hz, 1H), 7.83-7.98 (m, 2H), 7.62 (ddd, J=9.8, 8.5, 1.3 Hz, 1H), 7.27-7.51 (m, 6H), 6.40 (d, J=1.5 Hz, 1H). MS (ESI pos. ion) m/z: 445.9 (M+H).

Workup

  1. stirringAfter stirring for 24 h
  2. extractionThe aqueous solution was extracted with DCM (3×10 mL)
  3. washThe combined DCM layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17ec32542606434792c2a77da5657ad4
Source dataset
uspto-grants-2014_07
Patent number
US08778941B2

Reaction notes

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