Pyrrolidine → HCID 69266617, compound

HRID 751518Notes

Reaction equation

HRID 751518 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:18]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[C:19]=2[C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH2:34][CH2:35][CH2:36]OS(C)(=O)=O)[CH:26]=2)[C:12]2[O:16][CH:15]=[CH:14][C:13]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1>CN1CCCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:18]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[C:19]=2[C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH2:34][CH2:35][CH2:36][N:42]3[CH2:46][CH2:45][CH2:44][CH2:43]3)[CH:26]=2)[C:12]2[O:16][CH:15]=[CH:14][C:13]=2[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 86602344HCID 86602344, compound

Product 1

HCID 69266617HCID 69266617, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 84541-MethylpyrrolidineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

Dissolve methanesulfonic acid 3-{3-[4-(5-benzyloxybenzofur-7-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]indol-1-yl}propyl ester (220 mg, 0.39 mmol) and pyrrolidine (411 mg, 5.78 mmol) in 1-methylpyrrolidine (6 ml) and heat to 55° C. for 5 hours. Allow the reaction to cool to room temperature and stir overnight. Dilute the reaction in ethyl acetate, wash with water and brine, and dry with magnesium sulfate. Purification by flash chromatography gives the title compound (200 mg, 95%). MS(ES+): 546.13.

Workup

  1. customAllow the reaction
  2. temperatureto cool to room temperature
  3. additionDilute
  4. washwash with water and brine
  5. dry with materialdry with magnesium sulfate
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-65997ce13d2047af9cbb99c574ceac80
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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