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

HRID 1822823노트

반응식

HRID 1822823 반응식
[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

참가 물질

6

반응물 3

HCID 10942334Sodium Methoxide2회HCID 154044665-Mercapto-2-methyl-benzoic acidHCID 221704246-Bromo-n-(5-bromo-2-thiazolyl)pyridin-2-amine

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
54 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4919c2a4e5a04252ac2ddc5bacb192be
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037926B2

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