Water → [6-(2-Cylohexylsulfanyl-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine

HRID 1854604노트

반응식

HRID 1854604 반응식
Cl[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].[CH:27]1([SH:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.O>CC(O)C>[CH:27]1([S:33][C:2]2[O:3][C:4]([C:7]3[N:12]=[C:11]([NH:13][C:14]4[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=4)[CH:10]=[CH:9][CH:8]=3)=[CH:5][N:6]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15290CyclohexanethiolHCID 53311311HCID 53311311, 화합물

생성물 1

HCID 53312329[6-(2-Cylohexylsulfanyl-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine수율 71%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of [6-(2-chloro-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (50 mg, 0.174 mmol), K2CO3 (72 mg, 0.523 mmol) and cyclohexanethiol (64 μl, 0.523 mmol) in iPrOH (5 ml) were heated to reflux for 18 h. The cooled mixture was treated with water and extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure to a yellow gum. The gum was taken up in a minimum of DCM and precipitated with n-pentane to afford the title compound as a beige solid (45 mg, 71%). 1H NMR (300 MHz, DMSO-d6) δ 9.76 (s, 1H), 8.10 (s, 1H), 7.56-7.78 (m, 4H), 7.17 (d, J=5.9 Hz, 1H), 6.75 (s, 1H), 3.71 (m, 1H), 2.31 (s, 3H), 2.08 (m, 2H), 1.64 (m, 8H). (ESI+) m/z 367 (M+H)+.

후처리

  1. temperaturewere heated
  2. temperatureto reflux for 18 h
  3. extractionextracted with DCM
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure to a yellow gum
  7. customprecipitated with n-pentane

출처 및 근거

ORD 기록
ord-5842e570d1754d8080b0cedef6bdc4fc
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962665B2

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