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

HRID 2354095Notes

Reaction equation

HRID 2354095 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.Cl.[NH:15]1[CH2:19][CH2:18][C@@H:17]([NH:20][C:21]2[N:22]=[CH:23][C:24](/[CH:27]=[CH:28]/[C:29]([O:31][CH3:32])=[O:30])=[N:25][CH:26]=2)[CH2:16]1.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(Cl)(Cl)Cl.O>[C:1]1([CH2:11][N:15]2[CH2:19][CH2:18][C@@H:17]([NH:20][C:21]3[N:22]=[CH:23][C:24](/[CH:27]=[CH:28]/[C:29]([O:31][CH3:32])=[O:30])=[N:25][CH:26]=3)[CH2:16]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 61951-NaphthaldehydeHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67129309methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl)acrylate dihydrochloride

Product 1

HCID 67128817methyl (2E)-3-(5-{[(3R)-1-(1-naphthylmethyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-naphthaldehyde (143 μl), methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl}acrylate dihydrochloride (260 mg) and DIEA (282 μl) in dichloromethane (20 mL) was stirred at ambient temperature for 1 hour. After then, sodium triacetoxyborohydride (515 mg) was added and stirred overnight. Water and chloroform was added to the reaction mixture, and organic layer was separated. Aqueous layer was extracted twice with chloroform and combined organic layer was washed twice with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel to give methyl (2E)-3-(5-{[(3R)-1-(1-naphthylmethyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (480 mg).

Workup

  1. stirringstirred overnight
  2. customwas separated
  3. extractionAqueous layer was extracted twice with chloroform and combined organic layer
  4. washwas washed twice with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-188b74c2807944c387914ed15f1581ed
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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