4-Methylbenzaldehyde → HCID 86603652, compound

HRID 226339Notes

Reaction equation

HRID 226339 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:7]=[N:8][C:9]=1[NH:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.CCN(CC)CC.[CH3:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[Cl:3][C:4]1[CH:5]=[C:6](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:7]=[N:8][C:9]=1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:31][C:32]2[CH:39]=[CH:38][C:35]([CH3:36])=[CH:34][CH:33]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 77254-MethylbenzaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86603653HCID 86603653, compound

Product 1

HCID 86603652HCID 86603652, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of ethyl (2E)-3-[5-chloro-6-(4-piperidylamino)-3-pyridyl]acrylate dihydrochloride (710 mg) in CH2Cl2 (14 ml) was added Et3N(0.517 ml), the mixture was stirred at 23° C. for 30 minutes. To the mixture was added 4-Methyl-benzaldehyde (0.241 ml) and SODIUM triacetoxyborohydride (590 mg), the mixture was stirred at 23° C. for 24 hours. The reaction mixture was poured into sat.NaHCO3aq. (20 ml)-AcOEt (20 ml). The organic layer was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography eluted with 5% MeOH in dichloromethane to give ethyl (2E)-3-(5-chloro-6-{[1-(4-methylbenzyl)-4-piperidyl]amino}-3-pyridyl)acrylate (671 mg).

Workup

  1. stirringthe mixture was stirred at 23° C. for 24 hours
  2. additionThe reaction mixture was poured into sat.NaHCO3aq
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with 5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-9bf2dffdf02540498ec660735383778a
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

Loading…