Sodium Bicarbonate → 6-CHLORO-N-[5-(2-CYCLOPENTYLAMINO-4-PYRIDYL)-4-(3-METHYLPHENYL)-1,3-THIAZOL-2-YL]NICOTINAMIDE

HRID 1268739Notes

Reaction equation

HRID 1268739 reaction equation
[CH:1]1([NH:6][C:7]2[CH:12]=[C:11]([C:13]3[S:17][C:16]([NH2:18])=[N:15][C:14]=3[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][N:29]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH:18][C:16]2[S:17][C:13]([C:11]3[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:12]=3)=[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)[N:15]=2)=[O:33])=[CH:30][N:29]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 17862984HCID 17862984, compoundHCID 185485896-Chloropyridine-3-carbonyl chloride--hydrogen chloride (1/1)

Product 1

HCID 102066296-CHLORO-N-[5-(2-CYCLOPENTYLAMINO-4-PYRIDYL)-4-(3-METHYLPHENYL)-1,3-THIAZOL-2-YL]NICOTINAMIDEYield 43.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [5-(2-cyclopentylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine (0.50 g, 1.4 mmol) and 4-dimethylaminopyridine (0.052 g, 0.43 mmol) in N,N-dimethylacetamide (10 mL) was added 6-chloronicotinoyl chloride hydrochloride (0.46 g, 2.1 mmol), and the mixture was stirred at 80° C. for 14 hrs. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 4:1) and the resulting crystals were recrystallized from ethanol to give the title compound (0.30 g, yield 42%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate 4:1)
  6. customthe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-e9166156b8a941618c1abb54a1f342b6
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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