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

HRID 2229919ノート

反応式

HRID 2229919 の反応式
[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]([CH2:25][C:26]1[C:27]([CH3:35])=[C:28]([C:30]([CH3:34])=[CH:31][C:32]=1[CH3:33])[NH2:29])#[N:24].C(N(CC)CC)C.O>ClCCl.CN(C)C1C=CN=CC=1>[C:23]([CH2:25][C:26]1[C:27]([CH3:35])=[C:28]([NH:29][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:30]([CH3:34])=[CH:31][C:32]=1[CH3:33])#[N:24]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 105228213-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarbonyl chlorideHCID 108449753-Cyanomethyl-2,4,6-trimethylaniline

生成物 1

HCID 54326638N2-(3-cyanomethyl-2,4,6-trimethylphenyl)-3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarboxamide収率 41.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarbonyl chloride (0.49 g, 1.34 mmol) in dichloromethane (4 mL) was added 3-cyanomethyl-2,4,6-trimethylaniline (0.24 g, 1.34 mmol) at 0° C. Triethylamine (0.21 mL, 1.47 mmol) and 4-dimethylaminopyridine (16 mg, 0.13 mmol) were added. The mixture was stirred at room temperature for 2 hours, then mixed with water (10 mL). The organic material was separated, and the aqueous layer was extracted with dichloromethane (2×5 mL). The extracts were combined and washed with water (10 mL) and saturated sodium chloride (10 mL), dried (MgSO4), then concentrated. The residue was purified by flash chromatography (SiO2, hexane:ethyl acetate/3:1, then 1:1) to give N2-(3-cyanomethyl-2,4,6-trimethylphenyl)-3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarboxamide (0.28 g, 41%) as a yellow oil.

後処理

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

出典と根拠

ORDレコード
ord-24178d41909948ff9a5586ecd0bd8860
出典データセット
uspto-grants-2002_07
特許番号
US06420567B1

反応ノート

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