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

HRID 1959540

반응식

HRID 1959540 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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 extacted 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.

후처리

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

출처 및 근거

ORD 기록
ord-29e65dfde2af4f218760a448490490b6
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410160B2

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