1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl 3-{[2-(4-morpholinyl)ethyl]oxy}benzoate

HRID 884819

反応式

HRID 884819 の反応式
NC1N([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2C)[C:10]([OH:12])=[O:11])N=CC=1C(=O)C1C=CC=CC=1.[C:25]([O:29][C:30](=O)NN)([CH3:28])(C)C.CCN=C=NC[CH2:40][CH2:41][N:42]([CH3:44])C.[CH:45]1C=CC2N(O)N=NC=2[CH:50]=1.[Cl-].[Na+].[OH2:57]>CN(C=O)C>[CH2:45]([O:12][C:10](=[O:11])[C:9]1[CH:13]=[CH:14][CH:15]=[C:7]([O:57][CH2:40][CH2:41][N:42]2[CH2:28][CH2:25][O:29][CH2:30][CH2:44]2)[CH:8]=1)[CH3:50]

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 112094383-(5-amino-4-benzoyl-1H-pyrazol-1-yl)-4-methylbenzoic acidHCID 57417360Sodium chloride; water

生成物 1

HCID 58089039Ethyl 3-{[2-(4-morpholinyl)ethyl]oxy}benzoate収率 26%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To DMF (10 mL) at rt was added 3-(5-amino-4-benzoyl-pyrazol-1-yl)-4-methyl-benzoic acid 1 (0.50 g, 1.56 mmol, 1.0 eq), t-butylcarbazate (0.206 g, 1.56 mmol, 1.0 eq), EDCI (0.313 g, 1.63 mmol, 1.05 eq) and HOBt (0.238 g, 1.56 mmol, 1.0 eq). The reaction was stirred for 19 h, poured into brine (100 mL) and extracted with EtOAc (2×20 mL). The organic extracts were combined were washed with brine (1×20 mL). The brine layer was separated and extracted with EtOAc (1×10 mL). All organic extracts were combined dried over Na2SO4, filtered and concentrated in vacuo. This material was dissolved in CH2Cl2 (10 mL) and cooled to 0° C. TFA (3 mL) was added and the reaction mixture allowed to warm to rt over 2 h. The solvent was removed in vacuo to give crude solid which was triturated with EtOAc/ether (1/1) giving 2 (180 mg, 26%) as a light tan in color solid.

後処理

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe organic extracts were combined were washed with brine (1×20 mL)
  3. customThe brine layer was separated
  4. extractionextracted with EtOAc (1×10 mL)
  5. dry with materialAll organic extracts were combined dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThis material was dissolved in CH2Cl2 (10 mL)
  9. additionTFA (3 mL) was added
  10. temperatureto warm to rt over 2 h
  11. customThe solvent was removed in vacuo
  12. customto give crude solid which
  13. customwas triturated with EtOAc/ether (1/1)

出典と根拠

ORDレコード
ord-1354caac43864b2f8800989c17d8d958
出典データセット
uspto-grants-2012_08
特許番号
US08242117B2

関連ノート

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