Water → HCID 86642874, compound

HRID 1848859Notes

Reaction equation

HRID 1848859 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.Cl.Cl[CH2:15][C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C)C=O>[NH2:21][C:18]1[S:19][CH:20]=[C:16]([CH2:15][O:12][C:4]2[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])[N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 86642874HCID 86642874, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 4-fluoro-2-hydroxybenzoate (552 mg), 4-(chloromethyl)thiazol-2-amine hydrochloric acid (600 mg) and Cs2CO3 (2.64 g) in 15 mL N,N-dimethylformamide was stirred at room temperature for 24 hours. Water was added and the mixture was extracted with ethyl acetate (2×), washed with water (2×) and brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel using 10-50% ethyl acetate in hexanes as eluent.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×)
  2. washwashed with water (2×) and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using 10-50% ethyl acetate in hexanes as eluent

Sources & evidence

ORD record
ord-c4b819cad35845efa62469da13f1d62b
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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