Sodium Methoxide → 5-[[2-[N-(6-Bromopyridin-2-yl)amino]thiazol-5-yl]thio]-2-methylbenzoic acid

HRID 49142ノート

反応式

HRID 49142 の反応式
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[S:10][C:11](Br)=[CH:12][N:13]=2)[CH:5]=[CH:4][CH:3]=1.[C:15]([C:18]1[CH:19]=[C:20]([SH:25])[CH:21]=[CH:22][C:23]=1[CH3:24])([OH:17])=[O:16].C[O-].[Na+]>CO.C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[S:10][C:11]([S:25][C:20]3[CH:21]=[CH:22][C:23]([CH3:24])=[C:18]([CH:19]=3)[C:15]([OH:17])=[O:16])=[CH:12][N:13]=2)[CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 10942334Sodium Methoxide2 回HCID 154044665-Mercapto-2-methyl-benzoic acidHCID 221704246-Bromo-n-(5-bromo-2-thiazolyl)pyridin-2-amine

生成物 1

HCID 221703845-[[2-[N-(6-Bromopyridin-2-yl)amino]thiazol-5-yl]thio]-2-methylbenzoic acid収率 81.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
54 °C

実験手順

A suspension of 2-[(6-bromo-2-pyridinyl)amino]-5-bromothiazole (100 mg, 0.3 mmol), 3-carboxy-4-methylthiophenol (170 mg, 0.98 mmol) and sodium methoxide (210 μL, 25% w/w solution in methanol, 0.9 mmol) in methanol (4.9 mL) and THF (2 mL) was heated to 54° C. for 5.5 h. Supplemental sodium methoxide solution (1.42 mL) was added in portions over a period of 5 h. The mixture was heated to 54° C. for 16 h and concentrated. The residue was diluted with 1 N aqueous HCl solution at 0° C. and stirred for several minutes. The precipitated solid was filtered, washed several times with water and ether, and dried in vacuo over P2O5. Trituration with ether afforded the titled compound (103 mg, 81%) as an off-white solid.

後処理

  1. temperatureThe mixture was heated to 54° C. for 16 h
  2. concentrationconcentrated
  3. additionThe residue was diluted with 1 N aqueous HCl solution at 0° C.
  4. filtrationThe precipitated solid was filtered
  5. washwashed several times with water and ether
  6. dry with materialdried in vacuo over P2O5

出典と根拠

ORDレコード
ord-ef954bfc615b4c038770449f1a96e266
出典データセット
uspto-grants-2004_03
特許番号
US06706717B2

反応ノート

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