Triethylamine → 5-Chloro-n-(4,4-dimethyl-6,7-dihydro-4h-pyrano[4,3-d]thiazol-2-yl)-2-methoxybenzamide

HRID 538812Notes

Reaction equation

HRID 538812 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[S:9][C:8]([NH2:11])=[N:7][C:6]=2[CH2:5][CH2:4][O:3]1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:23][CH3:24])=[C:18]([CH:22]=1)[C:19](O)=[O:20].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C1COCC1.C([O-])(O)=O.[Na+]>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:23][CH3:24])=[C:18]([CH:22]=1)[C:19]([NH:11][C:8]1[S:9][C:10]2[C:2]([CH3:12])([CH3:1])[O:3][CH2:4][CH2:5][C:6]=2[N:7]=1)=[O:20]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 769705-Chloro-o-anisic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 871793724,4-dimethyl-4H,6H,7H-pyrano[4,3-d][1,3]thiazol-2-amine

Product 1

HCID 871795845-Chloro-n-(4,4-dimethyl-6,7-dihydro-4h-pyrano[4,3-d]thiazol-2-yl)-2-methoxybenzamideYield 78.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of Example 89E (1.0 g, 5.6 mmol) in THF (30 mL) were added 5-chloro-2-methoxy-benzoic acid (1.86 g, 10.0 mmol, Aldrich), N-(3-dimethylaminopropyl)-N-ethylcarbodimide hydrochloride (1.91 g, 10.0 mmol, Aldrich), 1-hydroxybenzotriazole (1.35 g, 10.0 mmol) and triethylamine (3.5 mL, 3.5 mmol, Aldrich). The mixture was stirred overnight at room temperature. The reaction mixture was then diluted with 1 M aqueous NaHCO3 (20 mL) and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, 0-5% methanol in dichloromethane to afford 1.55 g (78%) of the title compound. MS (ESI+) m/z 353 (M+H)+

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (2×30 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (SiO2, 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-0438e9ce93cf42c4881aa604fb5fdf3d
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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