Hydrochloric Acid → HCID 90072615, compound

HRID 521935Notes

Reaction equation

HRID 521935 reaction equation
[O:1]1[CH2:5][CH:4]=[C:3]([C:6]2[CH:11]=[C:10]([F:12])[C:9]([C:13]3[S:14][CH:15]=[C:16]([C:18]([O:20]C)=[O:19])[N:17]=3)=[C:8]([F:22])[CH:7]=2)[CH2:2]1.[Li+].[OH-].Cl>CO.C1COCC1.O.CCOC(C)=O>[F:12][C:10]1[CH:11]=[C:6]([CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)[CH:7]=[C:8]([F:22])[C:9]=1[C:13]1[S:14][CH:15]=[C:16]([C:18]([OH:20])=[O:19])[N:17]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86713872HCID 86713872, compound

Product 1

HCID 90072615HCID 90072615, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

This mixture was diluted with 30 mL MeOH and ran through an H-cube hydrogenator (1 mL/min, 60 bar, 70 deg C.) to provide, after concentration, methyl 2-(2,6-difluoro-4-(tetrahydrofuran-3-yl)phenyl)thiazole-4-carboxylate (44 mg). This ester was diluted with THF (3 mL) and water (1.5 mL) and LiOH (6.5 mg, 2.0 equiv.) was added. After stirring for 2.5 hours at rt, the mixture was neutralized with 1 N HCl(aq), diluted with EtOAc and washed with brine. The organic extracts were dried (Na2SO4) and concentrated in vacuo to provide the title compound (42 mg, quant).

Workup

  1. customran through an H-cube hydrogenator (1 mL/min, 60 bar, 70 deg C.)
  2. customto provide
  3. concentrationafter concentration, methyl 2-(2,6-difluoro-4-(tetrahydrofuran-3-yl)phenyl)thiazole-4-carboxylate (44 mg)
  4. additionwas added
  5. washwashed with brine
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d5305ee0812479e86097f0c6f9ba290
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

Loading…