2-Methoxybenzaldehyde → methyl (2E)-3-(5-{[(3R)-1-(2-methoxybenzyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate

HRID 226404Notes

Reaction equation

HRID 226404 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.C(N(CC)C(C)C)(C)C.[CH3:30][O:31][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][O:31][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 86582-MethoxybenzaldehydeHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67129309methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl)acrylate dihydrochloride

Product 1

HCID 86603714methyl (2E)-3-(5-{[(3R)-1-(2-methoxybenzyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylateYield 64.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl}acrylate dihydrochloride (260 mg) in CH2Cl2 (2.6 mL) was added N,N-diisopropylethylamine (282 uL), 2-methoxybenzaldehyde (121.2 mg), and sodium triacetoxyborohydride (343 mg), which was stirred at room temperature for 1 hour. To the resultant was added sat. 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 purified by column chromatography on silica gel to give methyl (2E)-3-(5-{[(3R)-1-(2-methoxybenzyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (193 mg) as a yellow amorphous.

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. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-809f4b162abb429d8f724c5793a259c0
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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