Lithium Hydroxide → 4-[(Dimethylamino)carbonyl]-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

HRID 2243027ノート

反応式

HRID 2243027 の反応式
[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[N:6]=[C:7]([C:15]2[CH:16]=[N:17][C:18]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:19][CH:20]=2)[S:8][C:9]=1[C:10]([O:12]CC)=[O:11])=[O:4].[OH-].[Li+]>CO>[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[N:6]=[C:7]([C:15]2[CH:16]=[N:17][C:18]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:19][CH:20]=2)[S:8][C:9]=1[C:10]([OH:12])=[O:11])=[O:4]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 25126467Ethyl 4-Dimethylcarbamoyl-2-[6-(3-ethyl-ureido)-pyridin-3-yl]-thiazole-5-carboxylate

生成物 1

HCID 592084804-[(Dimethylamino)carbonyl]-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid収率 35.48%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of ethyl 4-dimethylcarbamoyl-2-[6-(3-ethyl-ureido)-pyridin-3-yl]-thiazole-5-carboxylate (Example 52, 0.7 g, 1.78 mmol) in methanol (15 mL) was added 2 N lithium hydroxide (8 mL). The mixture was heated to 50° C. overnight. After completion of the reaction, the reaction mixture was concentrated to dryness. Water was added and the pH was adjusted with 2 N hydrochloric acid to pH 2. The precipitated solid was filtered and dried under vacuum to afford 0.2 g (35.48%) of the title compound as a pale brown solid. MS (APCI): 364 (M+H+) for C16H18N4O4S; NMR: δ 1.1 (t, 3H), δ 2.8 (s, 3H), δ 3.07 (s, 3H), δ 7.62 (d, 1H), δ 7.75 (br s, 1H), δ 8.25 (d, 1H), δ 8.82 (s, 1H), δ 9.55 (br s, 1H).

後処理

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated to dryness
  3. additionWater was added
  4. filtrationThe precipitated solid was filtered
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-994a09df5dc24cdb88269beb5091dfda
出典データセット
uspto-grants-2010_03
特許番号
US07674801B2

反応ノート

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