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1,1'-Carbonyldiimidazole → 2-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenethyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 560553
ノート
印刷プレビュー

反応式

HRID 560553 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19].[F:30][C:31]1[CH:45]=[CH:44][C:34]([CH2:35][CH2:36][NH:37][CH2:38][CH:39]([O:42][CH3:43])[O:40][CH3:41])=[CH:33][CH:32]=1>O1CCCC1>[CH3:43][O:42][CH:39]([O:40][CH3:41])[CH2:38][N:37]([CH2:36][CH2:35][C:34]1[CH:33]=[CH:32][C:31]([F:30])=[CH:45][CH:44]=1)[C:18](=[O:19])[NH:1][C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 627938962-amino-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideHCID 63686615N-(4-fluorophenethyl)-2,2-dimethoxyethanamine

生成物 1

HCID 866452872-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenethyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide収率 19%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of 2-amino-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide (0.50 g, 2.01 mmol) in tetrahydrofuran (30 mL) was added 1,1′-carbonyldiimidazole (0.39 g, 2.41 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 6 hours and N-(4-fluorophenethyl)-2,2-dimethoxyethanamine (0.59 g, 2.61 mmol) was added. The reaction mixture was stired for 17 hour at ambient temperature. The solvent was removed in vacuo, and the residue was purified by column chromatography eluted with dichloromethane/methanol (4/1) to afford 2-(3-(2,2-dimethoxyethyl)-3-(4-fluorophenethyl)ureido)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide as an oil in 19% yield (0.19 g): MS (ES+) m/z 502.4 (M+1).

後処理

  1. customThe resulting reaction mixture
  2. waitThe reaction mixture was stired for 17 hour at ambient temperature
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography
  5. washeluted with dichloromethane/methanol (4/1)

出典と根拠

ORDレコード
ord-819e1316bdbb46a78de9d4b8a8d52010
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08063084B2

反応ノート

読み込み中…

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