Hantzsch ester → HCID 178503147, compound

HRID 926556Notes

Reaction equation

HRID 926556 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH:16]=[C:15]2[OH:23].ClC1C2C(=CC=C(C(C3N(C)C(C)=NC=3)O)C=2)N=C(OC)C=1CC1C=NC(C(F)(F)F)=CC=1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>N1C=CC=CC=1>[Br:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([OH:22])[C:16]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1)=[C:15]2[OH:23]

Participants

6

Reactant 4

HCID 70849Hantzsch esterHCID 769854-(Methylthio)benzaldehydeHCID 546894466-Bromo-4-hydroxyquinolin-2(1H)-oneHCID 118005815(4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanol

Product 1

HCID 178503147HCID 178503147, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-(methylthio)benzaldehyde (3.00 g, 19.7 mmol), 6-bromo-4-hydroxyquinolin-2(1H)-one (4.72 g, 19.7 mmol, Intermediate 45: step a), diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (5.23 g, 20.7 mmol), and pyridine (100 mL) was stirred at 80° C. for 4 hours and then at room temperature overnight. The reaction was cooled and the formed precipitate was filtered, washed with Et2O (100 mL), and dried to afford the title compound as a white solid.

Workup

  1. customat room temperature
  2. customovernight
  3. temperatureThe reaction was cooled
  4. filtrationthe formed precipitate was filtered
  5. washwashed with Et2O (100 mL)
  6. customdried

Sources & evidence

ORD record
ord-845dfdbadfec47d8ae0aaff17523b971
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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