Potassium Carbonate → 3-(Pyridin-4-ylamino)-1H-indole-2-carboxylic Acid 2-piperidin-1-yl-ethyl Ester

HRID 1376122ノート

反応式

HRID 1376122 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([OH:19])=[O:18])=[CH:3][CH:2]=1.C(N(CC)C(C)C)C.[N:28]1([CH2:34][CH2:35]O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[N:28]1([CH2:34][CH2:35][O:18][C:17]([C:9]2[NH:10][C:11]3[C:16]([C:8]=2[NH:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:19])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 18232N-PiperidinoethanolHCID 521913N,N-Diethyl-2-propanamineHCID 101989283-(pyridin-4-ylamino)-1H-indole-2-carboxylic Acid

生成物 1

HCID 104288633-(Pyridin-4-ylamino)-1H-indole-2-carboxylic Acid 2-piperidin-1-yl-ethyl Ester収率 38.4%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
0 °C

実験手順

Stir under N2 at 0° C. a mixture of 3-(4-pyridinylamino)-1H-indole-2-carboxylic acid (0.25 g, 1 mmol), benzotriazol-1-yloxytris(pyrrlidino)-phosphonium hexafluorophosphate (0.52 g, 1 mmol), diethylisopropylamine (0.175 mL, 1 mmol) and 1-methyl-2-pyrrolidinone (4.0 mL). Add 1-piperidineethanol (0.50 mL, 3.8 mmol) in one portion and stir at ambient temperature for 18.5 h. Pour the reaction into 5% aqueous potassium carbonate and extract with ethyl acetate (2×20mL). Wash the combined extract with water (20 mL), brine (20 mL), dry over MgSO4, filter and concentrate under vacuum to a dark residue. Chromatograph over silica gel (Redisep cartridge, 30 g) and elute with a step gradient of 10% methanol/dichloromethane (150 mL) to 20% methanol/dichloromethane. Concentrate like fractions under vacuum to an oil. Dry the oil under high vacuum at ambient temperature and obtain 0.14 g of the title compound as a tan foam: MS 365(M+H), TLC (silica gel, 0.5/9.5/90 ammonium hydroxide/methanol/dichloromethane) Rf=0.25.

後処理

  1. additionPour
  2. extractionextract with ethyl acetate (2×20mL)
  3. washWash the
  4. extractioncombined extract with water (20 mL), brine (20 mL)
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate under vacuum to a dark residue
  8. washChromatograph over silica gel (Redisep cartridge, 30 g) and elute with a step gradient of 10% methanol/dichloromethane (150 mL) to 20% methanol/dichloromethane
  9. concentrationConcentrate like fractions under vacuum to an oil
  10. customDry the oil under high vacuum at ambient temperature

出典と根拠

ORDレコード
ord-093801581d6245fd9460e761f975258e
出典データセット
uspto-grants-2007_01
特許番号
US07169925B2

反応ノート

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