Triethylamine → (4-[(cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonate

HRID 1717321ノート

反応式

HRID 1717321 の反応式
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=3)[C:11]=2[CH2:12][OH:13])=[O:6])[CH2:3][CH2:2]1.[S:25](Cl)([CH3:28])(=[O:27])=[O:26].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[CH3:28][S:25]([O:13][CH2:12][C:11]1[N:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)[N:9]=[N:8][C:7]=1[C:5]([NH:4][CH:1]1[CH2:2][CH2:3]1)=[O:6])(=[O:27])=[O:26]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57665224N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(hydroxymethyl)-1H-1,2,3-triazole-4-carboxamide

生成物 1

HCID 86629804(4-[(cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)methyl methanesulfonate収率 94.7%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

N-Cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(hydroxymethyl)-1H-1,2,3-triazole-4-carboxamide (1.12 g, 3.39 mmol) obtained in Example 112 and mesyl chloride (0.293 ml, 3.73 mmol, 1.1 eq.) were dissolved in THF (22 ml), and a solution of triethylamine (0.615 ml, 4.41 mmol, 1.3 eq.) in THF (2 ml) was added dropwise over 10 min with stirring at 0° C. The reaction mixture was stirred at 0° C. for 50 min. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with 10% brine and saturated brine. The aqueous layers were each extracted with ethyl acetate (50 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated. Diethyl ether was added and the precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (1.31 g, 3.21 mmol, 94.6%).

後処理

  1. stirringThe reaction mixture was stirred at 0° C. for 50 min
  2. washwashed with 10% brine and saturated brine
  3. extractioneach extracted with ethyl acetate (50 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionDiethyl ether was added
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with diethyl ether
  9. customdried

出典と根拠

ORDレコード
ord-22f2b586f4df460ebfc8b35cdf5f2563
出典データセット
uspto-grants-2010_09
特許番号
US07803822B2

反応ノート

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