6-Chloronicotinoyl Chloride → 2-Chloro-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-5-carboxamide

HRID 1967731Notes

Reaction equation

HRID 1967731 reaction equation
[NH2:1][C:2]1[S:3][C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:5]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][N:20]=1>N1C=CC=CC=1>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:1][C:2]2[S:3][C:4]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)=[C:5]([C:7]3[O:8][CH:9]=[CH:10][CH:11]=3)[N:6]=2)=[O:24])=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 27821656-Chloronicotinoyl ChlorideHCID 231441582-Amino-4-(2-furyl)-5-morpholinothiazole

Product 1

HCID 231444172-Chloro-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-5-carboxamideYield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-4-(2-furyl)-5-morpholinothiazole (2.15 g, 8.57 mmol) obtained in Step 1 of Example 29 was dissolved in pyridine (25 mL), and 6-chloronicotinoyl chloride (1.81 g, 10.3 mmol) and N,N-dimethylaminopyridine (105 mg, 0.86 mmol) were added thereto. The mixture was stirred at room temperature for 10 hours, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:2) to afford the entitled Compound 32 (1.96 g, 59%).

Workup

  1. distillationthe solvent was distilled away under reduced pressure
  2. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:2)

Sources & evidence

ORD record
ord-a6a0f82c43b84523adcff6470b129d89
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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