Sodium hydride → [4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-(5-phenyl-thiazol-2-yl)-amine

HRID 1355507노트

반응식

HRID 1355507 반응식
[C:1]([SiH2:5][O:6][C:7]([CH3:16])([CH3:15])[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH2:14])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:20]1[S:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:23][N:24]=1>C1COCC1>[C:1]([SiH2:5][O:6][C:7]([CH3:16])([CH3:15])[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:23][N:24]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 217888402-Chloro-5-phenyl-1,3-thiazoleHCID 91865194HCID 91865194, 화합물

생성물 1

HCID 131723945[4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-(5-phenyl-thiazol-2-yl)-amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-2-ylamine (8-5), 1.00 g (4.19 mmol) was dissolved in 20 mL anhydrous THF at room temp, and NaH (60% dispersion, 0.670 g, 16.8 mmol) was added. When the bubbling stopped, 2-chloro-5-phenyl-thiazole (Hafez, E. A. A.; Abed, N. M.; Elsakka, I. A.; J. Heterocycl. Chem. 1983; 20, 285-288), 0.739 g (3.78 mmol) was added, and the reaction was heated to reflux. After 2 hours the THF was removed in vacuo and the resulting solution was taken to neutral pH with 1M HCl (aq) and filtered. The residue was purified by flash column chromatography using 20% EtOAc in hexane. 1H NMR (CDCl3): δ 9.09 (bs, 1H), 8.32 (d, 1H, J=5.2 Hz), 7.62 (s, 1H), 7.56 (d, 2H, J=7.4 Hz), 7.38 (t, 2H, J=7.6 Hz), 7.26 (overlapping with CHCl3, 1H), 6.90 (s, 1H), 6.82 (d, 1H, J=5.2 Hz), 4.75 (s, 2H), 0.96 (s, 9H), 0.14 (s, 6H). mp 207° C.

후처리

  1. addition20, 285-288), 0.739 g (3.78 mmol) was added
  2. temperaturethe reaction was heated to reflux
  3. customAfter 2 hours the THF was removed in vacuo
  4. filtrationfiltered
  5. customThe residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-9c74ecd4ea634fa1b9d7869adef5d750
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586424B2

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