Triethylamine → 2-(4-(4-methyl-5-(pyridin-3-ylmethylcarbamoyl)thiazol-2-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)ethyl methanesulfonate

HRID 2067642ノート

反応式

HRID 2067642 の反応式
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[N:7]([C:10]2[S:11][C:12]([C:16]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:6]=[N:5]1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>O1CCCC1.C(OCC)(=O)C>[CH3:33][S:34]([O:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[N:7]([C:10]2[S:11][C:12]([C:16](=[O:17])[NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[C:13]([CH3:15])[N:14]=2)[CH:6]=[N:5]1)(=[O:36])=[O:35]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 250966952-(1-(2-hydroxyethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

生成物 1

HCID 594812642-(4-(4-methyl-5-(pyridin-3-ylmethylcarbamoyl)thiazol-2-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)ethyl methanesulfonate収率 70%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To the solution of 2-(1-(2-hydroxyethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide (0.20 g, 0.56 mmol) and triethylamine (0.15 mL, 1.11 mmol) in anhydrous tetrahydrofuran (10 mL) was added dropwise methanesulfonyl chloride (0.08 g, 0.67 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 3 hours, diluted with ethyl acetate (15 mL) and washed with water and brine. The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to afford the title compound as a yellow solid in 70% yield (0.17 g): 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 8.55-8.51 (m, 1H), 8.31 (s, 1H), 7.72-7.66 (m, 1H), 7.31-7.25 (m, 1H), 6.26 (t, J=5.8 Hz, 1H), 4.60 (d, J=5.8 Hz, 2H), 4.54 (t, J=5.1 Hz, 2H), 4.19 (t, J=5.1 Hz, 2H), 3.02 (s, 3H), 2.65 (s, 3H); MS (ES+) m/z 439.2 (M+1).

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a039ba4f5fe74372bcc0cbe41411ff1a
出典データセット
uspto-grants-2012_10
特許番号
US08293768B2

反応ノート

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