Water → N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 2067505ノート

反応式

HRID 2067505 の反応式
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17]([N:19]([CH2:28][CH:29](OC)[O:30]C)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[O:18])=[N:13][C:12]=1[CH3:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.FC(F)(F)C(O)=O>O1CCCC1>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:29]([OH:30])[CH2:28][N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:17]2=[O:18])=[N:13][C:12]=1[CH3:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86645286N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorobenzyl)ureido)-4-methylthiazole-5-carboxamide

生成物 1

HCID 25095416N-benzyl-2-(3-(4-fluorobenzyl)-5-hydroxy-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-benzyl-2-(3-(2,2-dimethoxyethyl)-3-(4-fluorobenzyl)ureido)-4-methylthiazole-5-carboxamide (0.47 g, 0.96 mmol) in tetrahydrofuran (10 mL) was added water (5 mL) and trifluoroacetic acid (5 mL) at ambient temperature. The resulting reaction mixture was heated to reflux for 5 hours. The solvent was removed in vacuo and the residue was purified by column chromatography to afford the title compound in 76% yield (0.32 g): mp 133-134° C.; 1H NMR (300 MHz, CDCl3) δ 7.35-6.97 (m, 9H), 6.10 (t, J=5.7 Hz, 1H), 5.99 (d, J=5.9 Hz, 1H), 5.03 (s, 1H), 4.53 (d, J=5.7 Hz, 2H), 4.41 (s, 2H), 3.60-3.54 (m, 1H), 3.27-3.23 (m, 1H), 2.52 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.4, 162.1, 160.8, 157.0, 153.5, 152.4, 137.9, 131.1, 129.9, 128.7, 127.8, 117.9, 115.9, 115.7, 49.3, 46.6, 44.0, 17.0; MS (ES+) m/z 441.3 (M+1).

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 5 hours
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-3d6f9674ffbd48649859f5a90f33c8b0
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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