Sodium Iodide → Methyl 4-{[(4'-chloro-4-methylbiphenyl-3-yl)acetyl](prop-2-yn-1-yl)amino}-1,3-thiazole-5-carboxylate

HRID 625668Notes

Reaction equation

HRID 625668 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH2:15][C:16]([NH:18][C:19]3[N:20]=[CH:21][S:22][C:23]=3[C:24]([O:26][CH3:27])=[O:25])=[O:17])[CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[CH2:36](Br)[C:37]#[CH:38]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH2:15][C:16]([N:18]([CH2:38][C:37]#[CH:36])[C:19]3[N:20]=[CH:21][S:22][C:23]=3[C:24]([O:26][CH3:27])=[O:25])=[O:17])[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 89825919Methyl 4-{[(4'-chloro-4-methylbiphenyl-3-yl)acetyl]amino}-1,3-thiazole-5-carboxylate

Product 1

HCID 117857521Methyl 4-{[(4'-chloro-4-methylbiphenyl-3-yl)acetyl](prop-2-yn-1-yl)amino}-1,3-thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

600 mg (1.5 mmol) of methyl 4-{[(4′-chloro-4-methylbiphenyl-3-yl)acetyl]amino}-1,3-thiazole-5-carboxylate were dissolved in 20 ml of acetonitrile, and 1.2 g (3.7 mmol) of cesium carbonate, 449 mg (3 mmol) of sodium iodide and 0.33 ml (3 mmol, 80% pure) of propargyl bromide were added. The mixture was then stirred at RT for 12. The resulting suspension was filtered. The mother liquor was concentrated by evaporation. The residue was taken up in water and the solution was extracted with dichloromethane. The organic phase was dried and concentrated by evaporation. The residue was taken up in acetonitrile and chromatographed (acetonitrile/water (0.05% trifluoroacetic acid 20/80 to 100/0)). This gave 415 mg of methyl 4-{[(4′-chloro-4-methylbiphenyl-3-yl)acetyl](prop-2-yn-1-yl)amino}-1,3-thiazole-5-carboxylate.

Workup

  1. filtrationThe resulting suspension was filtered
  2. concentrationThe mother liquor was concentrated by evaporation
  3. extractionthe solution was extracted with dichloromethane
  4. customThe organic phase was dried
  5. concentrationconcentrated by evaporation
  6. customchromatographed (acetonitrile/water (0.05% trifluoroacetic acid 20/80 to 100/0))

Sources & evidence

ORD record
ord-5036f32b87a347a7833e5945416fe46c
Source dataset
uspto-grants-2016_04
Patent number
US09307767B2

Reaction notes

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