Benzaldehyde, (dimethylamino)- → methyl (2E)-3-[5-({(3R)-1-[2-(dimethylamino)benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]acrylate

HRID 2354088Notes

Reaction equation

HRID 2354088 reaction equation
Cl.Cl.[NH:3]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[N:10]=[CH:11][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])=[N:13][CH:14]=2)[CH2:4]1.CCN(C(C)C)C(C)C.[CH3:30][N:31]([CH3:40])[C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH:34]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:30][N:31]([CH3:40])[C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34][N:3]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[N:10]=[CH:11][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])=[N:13][CH:14]=2)[CH2:4]1

Participants

7

Reactant 5

HCID 34289Benzaldehyde, (dimethylamino)-HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67129309methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl)acrylate dihydrochloride

Product 1

HCID 67128674methyl (2E)-3-[5-({(3R)-1-[2-(dimethylamino)benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl}acrylate dihydrochloride (240 mg) in CH2Cl2 (2.4 mL) was added DIEA (260 uL), 2-(dimethylamino) benzaldehyde (122.6 mg), and sodium triacetoxyborohydride (317 mg), which was stirred at room temperature for 15 hours. To the resultant was added saturated NaHCO3 aq., which was stirred for 20 min. The mixture was extracted with CH2Cl2. The organic phase was washed with brine and dried over Na2SO4, filtered, and evaporated in vacuo. The residue was washed with hexane to give methyl (2E)-3-[5-({(3R)-1-[2-(dimethylamino)benzyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]acrylate as a beige powder.

Workup

  1. stirringwas stirred for 20 min
  2. extractionThe mixture was extracted with CH2Cl2
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-c58cd4a93a0d43f38f5e7e4bcd861dbc
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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