Dimethyl Disulfide → 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(methylthio)pyridin-2-amine

HRID 1426091노트

반응식

HRID 1426091 반응식
Cl.[CH2:2]([O:9][C:10]1[C:11]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:12][CH:13]=[C:14](Br)[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Li]C.C([Li])CCC.[CH3:31][S:32]SC.[Cl-].[NH4+]>C1COCC1>[CH2:2]([O:9][C:10]1[C:11]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:12][CH:13]=[C:14]([S:32][CH3:31])[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

7

반응물 5

HCID 12232Dimethyl DisulfideHCID 25517Ammonium ChlorideHCID 160614653-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideHCID 178418339ButyllithiumHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 592256943-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(methylthio)pyridin-2-amine수율 74.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (prepared according to Example 1; 0.250 g, 0.664 mmol) was added to THF (30 mL) and cooled to −78° C. MeLi (0.519 mL, 0.831 mmol) was slowly added, and the reaction mixture was stirred for 10 minutes. Butyllithium (0.332 mL, 0.831 mmol) was added, and the reaction mixture was stirred for 15 minutes. 1,2-Dimethyldisulfane (0.438 g, 4.65 mmol) was added, and the reaction mixture was stirred for 15 minutes. Ammonium chloride was added, and the reaction mixture was extracted with CH2Cl2. The organic layer was purified by silica gel (10-20% EtOAc in hexanes) to give 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(methylthio)pyridin-2-amine (0.170 g, 74.5% yield). A portion of this compound was dissolved in dichloromethane, 2M HCl in ether was added, and the mixture was concentrated to give the title compound. 1H NMR (CDCl3) δ 12.30 (bs, 1H), 7.84 (m, 1H), 7.57 (d, 2H), 7.39 (m, 2H), 7.32 (m, 1H), 7.15 (m, 1H), 6.38 (s, 1H), 5.35 (s, 2H), 2.45 (s, 3H), 2.43 (s, 3H). Mass spectrum (apci) m/z=344.0 (M+H-HCl).

후처리

  1. stirringthe reaction mixture was stirred for 15 minutes
  2. stirringthe reaction mixture was stirred for 15 minutes
  3. extractionthe reaction mixture was extracted with CH2Cl2
  4. customThe organic layer was purified by silica gel (10-20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-92e402e0b7974ddca705c488a6a6ea02
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933077B2

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