1-Pyrrolidineethanamine → HCID 66772212, compound

HRID 1645264Notes

Reaction equation

HRID 1645264 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]([OH:23])=O)[O:5][C:6]=1[CH:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:48]1([CH2:53][CH2:54][NH2:55])[CH2:52][CH2:51][CH2:50][CH2:49]1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]([NH:55][CH2:54][CH2:53][N:48]2[CH2:52][CH2:51][CH2:50][CH2:49]2)=[O:23])[O:5][C:6]=1[CH:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17]

Participants

8

Reactant 5

HCID 13441-PyrrolidineethanamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66772119HCID 66772119, compound

Product 1

HCID 66772212HCID 66772212, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-methyl-5-((2-oxoindolin-3-ylidene)methyl)furan-2-yl)benzoic acid (40 mg, 0.12 mol) and HOBt (32 mg, 0.24 mol) in DMF (0.5 mL) was added EDCI (46 mg, 0.24 mmol). The reaction was stirred at rt for 10 min and then added 2-(pyrrolidin-1-yl)ethanamine (0.05 mL) followed by DIEA (0.05 mL). The reaction mixture was stirred at rt for 1 h and diluted with H2O (10 mL). The mixture was extracted with EtOAc (3×20 mL), dried over Na2SO4 and concentrated. The crude was purified by prep TLC (5%/MeOH, 1% TEA/DCM) to give 3-(4-methyl-5-((2-oxoindolin-3-ylidene)methyl)furan-2-yl)-N-(2-(pyrrolidin-1-yl)ethyl)benzamide (25 mg) LCMS (ES): m/z 442 [M+1]+.

Workup

  1. stirringThe reaction mixture was stirred at rt for 1 h
  2. extractionThe mixture was extracted with EtOAc (3×20 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude was purified by prep TLC (5%/MeOH, 1% TEA/DCM)

Sources & evidence

ORD record
ord-ad23e28f4d8248d089bdf183e131f769
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

Loading…