Water → N2-(3-acetoxymethyl-2,4,6-trimethylphenyl)-3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarboxamide

HRID 987853Notes

Reaction equation

HRID 987853 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([N:8]([CH2:20][O:21][CH3:22])[S:9]([C:12]2[CH:16]=[CH:15][S:14][C:13]=2[C:17](Cl)=[O:18])(=[O:11])=[O:10])[O:4][N:3]=1.[C:23]([O:26][CH2:27][C:28]1[C:29]([CH3:37])=[C:30]([C:32]([CH3:36])=[CH:33][C:34]=1[CH3:35])[NH2:31])(=[O:25])[CH3:24].C(N(CC)CC)C.O>ClCCl.CN(C)C1C=CN=CC=1>[C:23]([O:26][CH2:27][C:28]1[C:29]([CH3:37])=[C:30]([NH:31][C:17]([C:13]2[S:14][CH:15]=[CH:16][C:12]=2[S:9]([N:8]([C:5]2[O:4][N:3]=[C:2]([CH3:1])[C:6]=2[CH3:7])[CH2:20][O:21][CH3:22])(=[O:11])=[O:10])=[O:18])[C:32]([CH3:36])=[CH:33][C:34]=1[CH3:35])(=[O:25])[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 105228213-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarbonyl chlorideHCID 106559423-Acetoxymethyl-2,4,6-trimethylaniline

Product 1

HCID 54548392N2-(3-acetoxymethyl-2,4,6-trimethylphenyl)-3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarboxamideYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarbonyl chloride (1.1 g, 2.97 mmol) in dichloromethane (9 mL) was added 3-acetoxymethyl-2,4,6-trimethylaniline (0.6 g, 2.97 mmol) at 0° C. Triethylamine (0.46 mL, 3.26 mmol) and 4-dimethylaminopyridine (36 mg, 0.30 mmol) were added. The mixture was stirred at room temperature overnight, then mixed with water (10 mL). The organic material was separated, and the aqueous layer was extracted with dichloromethane (2×10 mL). The extracts were combined and washed with water (20 mL) and saturated sodium chloride (20 mL), dried (MgSO4), then concentrated. The residue was purified by flash chromatography (SiO2, hexane:ethyl acetate/2:1) to give N2-(3-acetoxymethyl-2,4,6-trimethylphenyl)-3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarboxamide (0.79 g, 50%) as a yellow oil.

Workup

  1. customThe organic material was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (2×10 mL)
  3. washwashed with water (20 mL) and saturated sodium chloride (20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (SiO2, hexane:ethyl acetate/2:1)

Sources & evidence

ORD record
ord-4b9b10fcafa24830a4578a1ce029d4b1
Source dataset
uspto-grants-2003_10
Patent number
US06632829B2

Reaction notes

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