Triethylamine → (7-Methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1lambda6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester

HRID 421508

反応式

HRID 421508 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]=1[S:7]([NH2:10])(=[O:9])=[O:8].[CH2:16]([O:18][C:19](=[O:28])[CH:20]=[C:21](OCC)OCC)[CH3:17].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH2:16]([O:18][C:19](=[O:28])[CH2:20][C:21]1[NH:1][C:2]2[S:3][CH:4]=[C:5]([CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]=2[S:7](=[O:8])(=[O:9])[N:10]=1)[CH3:17]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 1693882-Propenoic acid, 3,3-diethoxy-, ethyl esterHCID 574551872-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamide

生成物 1

HCID 58000246(7-Methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1lambda6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester収率 52.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

To a solution of 2-amino-4-methoxymethoxymethyl-thiophene-3-sulfonic acid amide (0.76 g, 3.01 mmol) in N,N-dimethylformamide (10 mL) at 25° C. was added 3,3-diethoxy-acrylic acid ethyl ester (0.68 g, 3.61 mmol). The reaction was stirred at 70° C. for 5 h before triethylamine (1.68 mL, 12.04 mmol) was added to the mixture. The reaction was stirred at 70° C. overnight. It was then cooled to 25° C., diluted with ethyl acetate (10 mL) and washed with 1.0 M aqueous hydrochloric acid solution (10 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified via flash column chromatography (Teledyne Isco RediSep column; 0-80% ethyl acetate in hexanes) to afford the desired product, (7-methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester (0.55 g, 1.57 mmol, 52%), as a brown oil. 1H NMR (400 MHz, CDCl3) δ: 1.32 (3H, t, J=7.2 Hz), 3.42 (3H, s), 3.68 (2H, s), 4.26 (2H, q, J=7.2 Hz), 4.76 (2H, s), 4.80 (2H, s), 7.00 (1H, s), 8.00 (1H, s).

後処理

  1. additionwas added to the mixture
  2. temperatureIt was then cooled to 25° C.
  3. washwashed with 1.0 M aqueous hydrochloric acid solution (10 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via flash column chromatography (Teledyne Isco RediSep column; 0-80% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-8ca68e532eb849828dfa576184ca2ce8
出典データセット
uspto-grants-2012_01
特許番号
US08097613B2

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