Water → HCID 69433893, compound

HRID 404915Notes

Reaction equation

HRID 404915 reaction equation
Cl[C:2]1[S:3][C:4]([C:7]#[N:8])=[CH:5][N:6]=1.[C:9]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O>[C:7]([C:4]1[S:3][C:2]([O:23][C:20]2[CH:19]=[CH:18][C:17]([NH:16][C:9](=[O:10])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[CH:22][CH:21]=2)=[N:6][CH:5]=1)#[N:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14852222-Chlorothiazole-5-carbonitrileHCID 2756771N-Boc-4-hydroxyaniline

Product 1

HCID 69433893HCID 69433893, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-chloro-thiazole-5-carbonitrile (900 mg 6.2 mmol; prepared according to procedure described in WO 01/17995, p. 103) and N-Boc-4-hydroxy-aniline (1.3 g, 6.2 mmol) were combined in N,N-dimethyl formamide (5 mL). To this solution, K2CO3 (2.6 g, 18.8 mmol) was added and the resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was then poured into water and extracted with ethyl acetate (2×). The combined organics were dried (Na2SO4), filtered and concentrated by rotary evaporation. The residue was purified by flash column chromatography (ethyl acetate:hexanes: 5%-50% ethyl acetate gradient) to give the title compound (2.0 g, 6.2 mmol, 100%) as a white solid. MS (ESI APCI) m/z 316.0 (M−H+); 1H NMR (300 MHz, DMSO-d6) δ 9.59 (s, 1H) 8.24 (s, 1H) 7.58 (d, J=9.0 Hz, 2H) 7.36 (d, J=9.0 Hz, 2H) 1.48 (s, 9H).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue was purified by flash column chromatography (ethyl acetate:hexanes: 5%-50% ethyl acetate gradient)

Sources & evidence

ORD record
ord-259c9ce58ed748698dcba416410cf2a7
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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