Picolinic acid → HCID 56943044, compound

HRID 341411Notes

Reaction equation

HRID 341411 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(C1NC=CN=1)(C1NC=CN=1)=O.[C:22]1([NH:28][C:29]2[N:34]=[C:33]([NH2:35])[N:32]=[C:31]([C:36]3[N:40]=C(C4SC=CN=4)O[N:37]=3)[N:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[C:22]1([NH:28][C:29]2[N:34]=[C:33]([NH2:35])[N:32]=[C:31]([C:36]3[N:37]=[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[O:9][N:40]=3)[N:30]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 1018Picolinic acid2×HCID 5250894Bis-(1H-imidazol-2-YL)-methanone2×HCID 66802785HCID 66802785, compound

Product 1

HCID 56943044HCID 56943044, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A mixture of picolinic acid (90 mg, 0.73 mmol) and carbonyl di-imidazole (0.12 g, 0.73 mmol) in pyridine (1 ml) was stirred for 2 h. N-Phenyl-6-(5-thiazol-2-yl-[1,2,4]oxadiazol-3-yl)-[1,3,5]triazine-2,4-diamine (prepared in an analogous manner to Intermediate 4, 100 mg, 0.41 mmol) was added and the resulting mixture was heated to 100 C and stirred for 24 h. In a separate vessel, a second mixture of picolinic acid (90 mg, 0.73 mmol) and carbonyl di-imidazole (0.12 g, 0.73 mmol) in pyridine (1 ml) was stirred for 90 minutes and added to the first mixture, which was stirred for a further 24 h at 100 C. The mixture was cooled to room temperature, concentrated under vacuum and suspended in aqueous sodium hydrogencarbonate solution. The solid was filtered off, washed with water, ethyl acetate and methanol and dried under vacuum to give the title compound (73 mg, 54%).

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated to 100 C
  3. stirringstirred for 24 h
  4. stirringwas stirred for 90 minutes
  5. additionadded to the first mixture, which
  6. stirringwas stirred for a further 24 h at 100 C
  7. concentrationconcentrated under vacuum
  8. filtrationThe solid was filtered off
  9. washwashed with water, ethyl acetate and methanol
  10. customdried under vacuum

Sources & evidence

ORD record
ord-15e0e5cd05494d84bcfe85bff5c02501
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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