Hydrochloric Acid → N-[(1R)-1-(5-hydroxypyridine-2-yl)ethyl]-2-(4-isopropylphenyl)acetamide

HRID 2383527

反応式

HRID 2383527 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C@@H:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][N:17]=2)[CH3:15])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C-]#N.[Na+].Cl>CS(C)=O.C(Cl)Cl.O>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([C@H:14]([NH:13][C:11](=[O:12])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=2)[CH3:15])=[N:17][CH:18]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 247654842-(4-isopropylphenyl)-N-[(1R)-1-(5-methoxypyridin-2-yl)ethyl]acetamide

生成物 1

HCID 24765483N-[(1R)-1-(5-hydroxypyridine-2-yl)ethyl]-2-(4-isopropylphenyl)acetamide

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
175 °C

実験手順

2-(4-Isopropylphenyl)-N-[(1R)-1-(5-methoxypyridin-2-yl)ethyl]acetamide (3.8 g, 12.2 mmol) (Example 11) was dissolved in DMSO (20 mL) and transferred to a sealed tube. To this solution was added NaCN (3.6 g, 73.0 mmol) and the mixture was stirred at 175° C. for 16 h. The mixture was cooled to room temperature and diluted with CH2Cl2 (200 mL) and water (100 mL). The pH of the aqueous layer was brought to neutral by the addition of 2N HCl and the layers were separated. The organic layer was washed with water (100 mL) and brine (100 mL), concentrated, and purified by normal phase chromatography (2-10% MeOH/CH2Cl2) to give N-[(1R)-1-(5-hydroxypyridine-2-yl)ethyl]-2-(4-isopropylphenyl)acetamide as a tan solid. 1H NMR (CDCl3, 400 MHz) δ 8.06 (t, J=1.65 Hz, 1H), 7.17 (m, 4H), 7.02 (m, 2H), 6.67 (d, J=7.50 Hz, 1H), 5.03 (quint., J=6.96 Hz, 1H), 3.53 (d, J=2.20 Hz, 2H), 2.88 (sept., J=6.69 Hz, 1H), 1.38 (d, J=6.77 Hz, 3H), 1.23 (d, J=6.95, 6H); MS (Electrospray): m/z 299.3 (M+H).

後処理

  1. customtransferred to a sealed tube
  2. temperatureThe mixture was cooled to room temperature
  3. customthe layers were separated
  4. washThe organic layer was washed with water (100 mL) and brine (100 mL)
  5. concentrationconcentrated
  6. custompurified by normal phase chromatography (2-10% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-8e81865dcf264317a176bade9c5753d4
出典データセット
uspto-grants-2012_09
特許番号
US08263627B2

関連ノート

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