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

HRID 1361754Notes

Reaction equation

HRID 1361754 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-41b0cba7f29348c48d86c76d3a789d1d
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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