Benzenepropanal → HCID 67128662, compound

HRID 2354100Notes

Reaction equation

HRID 2354100 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7]2[N:8]=[CH:9][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])=[N:11][CH:12]=2)[CH2:2]1.[CH3:19]CN(C(C)C)C(C)C.[C:28]1([CH2:34][CH2:35][CH:36]=O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCl>[C:28]1([CH2:34][CH2:35][CH2:36][N:1]2[CH2:5][CH2:4][CH2:19][C@@H:3]([NH:6][C:7]3[N:8]=[CH:9][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])=[N:11][CH:12]=3)[CH2:2]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 5

HCID 7707BenzenepropanalHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67128828HCID 67128828, compound

Product 1

HCID 67128662HCID 67128662, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl}acrylate (335 mg) in dichloromethane (5 mL) was added DIEA (870 uL), 3-phenylpropanal (157 ul), and sodium triacetoxyborohydride (424 mg), and the reaction mixture was stirred at ambient temperature for 2 hours. To the resultant was added saturated aq.NaHCO3, which was stirred for 30 min. The mixture was extracted with dichloromethane. The organic phase was washed with brine and dried over MgSO4, filtered, and evaporated in vacuo. The residue was crystallized from acetone and IPE to give methyl (2E)-3-[5-[{(3R)-1-(3-phenylpropyl)-3-piperidinyl}amino]-2-pyrazinyl]acrylate (183 mg) as a pale yellow crystal. The filtrate was evaporated and the residue was column chromatographed on silica gel (hexane:AcOEt=25:75) to give 84 mg of product.

Workup

  1. additionTo the resultant was added saturated aq
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was crystallized from acetone and IPE

Sources & evidence

ORD record
ord-2ef6525fe60244ad9b7c87338df0cf90
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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