1-Pyrrolidineethanamine → HCID 59190179, compound

HRID 1645257Notes

Reaction equation

HRID 1645257 reaction equation
[O:1]=[C:2]1[NH:3][C:4]2[C:9](/[C:10]/1=[CH:11]\[C:12]1[O:16][C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([O-:22])=O)=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:47]1([CH2:52][CH2:53][NH2:54])[CH2:51][CH2:50][CH2:49][CH2:48]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[O:1]=[C:2]1[NH:3][C:4]2[C:9](/[C:10]/1=[CH:11]\[C:12]1[O:16][C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([NH:54][CH2:53][CH2:52][N:47]3[CH2:51][CH2:50][CH2:49][CH2:48]3)=[O:22])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

8

Reactant 5

HCID 13441-PyrrolidineethanamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1750280HCID 1750280, compound

Product 1

HCID 59190179HCID 59190179, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of (E)-3-(5-((2-oxoindolin-3-ylidene)methyl)furan-2-yl)benzoate (20 mg, 0.06 mmol) and HOBt (16 mg, 0.14 mmol) in NMP (0.5 mL) was added EDCI (22 mg, 0.12 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 RHPLC to give (E)-3-(5-((2-oxoindolin-3-ylidene)methyl)furan-2-yl)-N-(2-(pyrrolidin-1-yl)ethyl)benzamide. LCMS (ES): m/z 463 [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 RHPLC

Sources & evidence

ORD record
ord-79c6133774a245879086ebc26587c539
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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