Ethanol → HCID 19012373, compound

HRID 1729339Notes

Reaction equation

HRID 1729339 reaction equation
[CH2:1]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])=[CH:14][CH:13]=2)[C:9](=[O:26])[C:8]([CH:27]=O)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH:29]([NH2:32])([CH3:31])[CH3:30].C(O)C.[BH3-]C#N.[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].O>[CH2:1]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])=[CH:14][CH:13]=2)[C:9](=[O:26])[C:8]([CH2:27][NH:32][CH:29]([CH3:31])[CH3:30])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 702EthanolHCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydrideHCID 19012335HCID 19012335, compound

Product 1

HCID 19012373HCID 19012373, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolvent

Procedure

A mixture of 3.7 g of 6-butyl-1-(2'-cyanobiphenyl-4-ylmethyl)-3-formyl-1,2-dihydro-2-oxopyridine, 0.59 g of isopropylamine and 3.55 g of titanium tetraisopropoxide is stirred for 2 hours at 20° under N2. 10 ml of absolute ethanol and then 610 mg of NaBH3CN are added, the mixture is stirred for a further 20 hours, 2 ml of water are then added and the mixture is filtered. The filtrate is evaporated. 6-Butyl-1-(2'-cyanobiphenyl-4-ylmethyl)-3-isopropylaminomethyl-1,2-dihydro-2-oxopyridine is obtained after conventional working-up.

Workup

  1. stirringthe mixture is stirred for a further 20 hours
  2. filtrationthe mixture is filtered
  3. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-b7c90d4499e94692a1f2db23b277dd2c
Source dataset
uspto-grants-1994_07
Patent number
US05332750

Reaction notes

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