2-Phenylpropanal → HCID 178435921, compound

HRID 931242Notes

Reaction equation

HRID 931242 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[CH2:12]2)=[N:8][C:9]=1[NH2:10].C(N(CC)CC)C.[C:31]1([CH:37]([CH3:40])[CH:38]=O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(O)C>[C:31]1([CH:37]([C:40]2[NH:10][C:9]3=[N:8][C:7]([N:11]4[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]5[CH2:23][CH2:22][CH2:21][CH2:20]5)=[O:18])[CH2:12]4)=[CH:6][CH:5]=[C:4]3[N:3]=2)[CH3:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 71462-PhenylpropanalHCID 8471TriethylamineHCID 89854051(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride2×

Product 1

HCID 178435921HCID 178435921, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride (Intermediate 1) (0.5 g, 1.7 mmol) in ethanol (20 mL) was added triethylamine (1 mL) and 2-phenylpropanal (0.25 g, 1.9 mmol). The reaction mixture was heated at reflux for 12 h. The mixture was then concentrated under reduced pressure, diluted with ice cold water and extracted with ethyl acetate. The organic layers were dried, filtered and concentrated, and the resulting residue was purified by preparative TLC to afford the title compound (65 mg, 9%). MS (ES+APCI) (M+H) 404.2; LCMS retention time 2.206 min (Method Y).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 12 h
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. additiondiluted with ice cold water
  5. extractionextracted with ethyl acetate
  6. customThe organic layers were dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-4761adc9e84547b0a48257f26414f3af
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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