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

HRID 1854604ノート

反応式

HRID 1854604 の反応式
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

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15290CyclohexanethiolHCID 53311311HCID 53311311、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-5842e570d1754d8080b0cedef6bdc4fc
出典データセット
uspto-grants-2015_02
特許番号
US08962665B2

反応ノート

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