Triethylamine → Ethyl 2-(isonicotinamido)-4-methylthiazole-5-carboxylate

HRID 45403

反応式

HRID 45403 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.C(N(CC)CC)C.Cl.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>O1CCCC1>[C:21]([NH:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylateHCID 12262826Isonicotinoyl chloride hydrochloride

生成物 1

HCID 719362Ethyl 2-(isonicotinamido)-4-methylthiazole-5-carboxylate収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (5.70 g, 30.60 mmol) and triethylamine (10.0 mL, 71.80 mmol) in tetrahydrofuran (100 mL) was added isonicotinoyl chloride hydrochloride (6.00 g, 32.00 mmol). The reaction mixture was stirred at ambient temperature for 2 days. The solvent was removed by evaporation and the resulting white solid was washed sequentially with water, 10% sodium bicarbonate solution, and water, then dried to afford the title compound in 90% yield (8.10 g); 1H NMR (DMSO-d6, 300 MHz) δ 8.77 (d, J=6.0 Hz, 2H), 8.77 (d, J=6.0 Hz, 2H), 4.23 (q, J=7.2 Hz, 2H), 2.34 (s, 3H). 1.27 (t, J=7.2 Hz, 3H); MS (ES+) m/z 292.0 (M+1).

後処理

  1. customThe solvent was removed by evaporation
  2. washthe resulting white solid was washed sequentially with water, 10% sodium bicarbonate solution, and water
  3. customdried

出典と根拠

ORDレコード
ord-2a7f7b852a024355ba6a8f13ce27cd05
出典データセット
uspto-grants-2013_09
特許番号
US08541457B2

関連ノート

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