1-Pyrrolidineethanamine → HCID 10050407, compound

HRID 1270984Notes

Reaction equation

HRID 1270984 reaction equation
[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:29])[NH:9][C:10]2([CH:17](C)[C:18]([NH:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:19])[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH2:11]2)=[CH:3][CH:2]=1.[C:36]1(C2C=CC=CC=2)C=CC(NC(=O)NC(C2C=CC(C)=CC=2)CC(O)=O)=CC=1.N1(CCN)CCCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:2]=[CH:3][C:4]([NH:7][C:8](=[O:29])[NH:9][C@@H:10]([C:15]2[CH:36]=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=2)[CH2:17][C:18]([NH:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:19])=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 13441-PyrrolidineethanamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184502433-(3-Biphenyl-4-yl-ureido)-3-p-tolyl-propionic acidHCID 69431468HCID 69431468, compound

Product 1

HCID 10050407HCID 10050407, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(3-Biphenyl-4-yl-ureido)-N-(2-pyrrolidin-1-yl-ethyl)-3-tolyl-propionamide. To a solution of 3-(3-biphenyl-4-yl-ureido)-3-p-tolyl-propionic acid (0.15 g, 0.40 mmol), 2-pyrrolidin-1-yl-ethylamine (0.05 g, 0.40 mmol) and HOBt (0.081 g, 0.60 mmol) in DMF (4 mL), was added EDCl (0.12 g, 0.60 mmol). The resulting solution was stirred under N2 at rt for 20 h. The solution was diluted with H2O (20 mL) and extracted with EtOAc (3×30 mL). The combined extracts were washed with brine (40 mL), dried (Na2SO4), and filtered, and the solvent was removed. The crude product was purified by column chromatography on silica gel using a gradient of 0–20% (MeOH(1% NH4OH)/CH2Cl2) to afford 0.12 g (63%) of the desired product as a white solid. Racemic compound: Rf=0.11 (10% MeOH (1% NH4OH)/CH2Cl2). MS (electrospray): mass calculated for C29H34N4O2, 470.27; m/z found, 471.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.57–7.50 (m, 4H), 7.43–7.37 (m, 4H), 7.29–7.25 (m, 3H), 7.16 (d, J=7.9 Hz, 2H), 5.22 (t, J=6.9 Hz, 1H), 3.28–3.23 (m, 2H), 2.68 (d, J=6.4 Hz, 2H), 2.52–2.48 (m, 6H), 2.31 (s, 3H), 1.77–1.75 (m, 4H).

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined extracts were washed with brine (40 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was removed
  6. customThe crude product was purified by column chromatography on silica gel using a gradient of 0–20% (MeOH(1% NH4OH)/CH2Cl2)

Sources & evidence

ORD record
ord-f5281460bdb54dd7b86c787b843ba61b
Source dataset
uspto-grants-2007_04
Patent number
US07202269B2

Reaction notes

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