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

HRID 2354088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354088
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

Komponenten

7

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c58cd4a93a0d43f38f5e7e4bcd861dbc
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750155B2

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