2-(3-Hydroxy-2-pyridyl)-4-thiazolecarboxylic acid → HCID 178522729, compound

HRID 1638322Notes

Reaction equation

HRID 1638322 reaction equation
[OH:1][C:2]1[C:3]([C:8]2[S:9][CH:10]=[C:11]([C:13]([OH:15])=O)[N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1>CN(C=O)C>[OH:1][C:2]1[C:3]([C:8]2[S:9][CH:10]=[C:11]([C:13]([NH:16][C:17]3[NH:21][N:20]=[N:19][N:18]=3)=[O:15])[N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1362052682-(3-Hydroxy-2-pyridyl)-4-thiazolecarboxylic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178522729HCID 178522729, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A suspension of 2-(3-hydroxy-2-pyridyl)-4-thiazolecarboxylic acid (200 mg) and N,N'-carbonyldiimidazole (hereinafter, referred to as CDI) (291.9 mg) in dry DMF (7 ml), prepared under argon atmosphere, was heated at 80° C. for 1.5 hours. A solution of 5-aminotetrazole (91.9 mg) in dry DMF (3 ml) was added dropwise thereto and allowed to react at 85° C. for 3.5 hours. Then the reaction mixture was cooled to room temperature. The produced solids were filtered with suction, washed with DMF and THF and dried to give white solids of 2-(3-hydroxy-2-pyridyl)-N-(1H-tetrazole-5-yl)-4-thiazolecarboxamide (140 mg, 54%), m.p. above 300° C.

Workup

  1. customprepared under argon atmosphere
  2. customto react at 85° C. for 3.5 hours
  3. temperatureThen the reaction mixture was cooled to room temperature
  4. filtrationThe produced solids were filtered with suction
  5. washwashed with DMF and THF
  6. customdried

Sources & evidence

ORD record
ord-c578c7d5c256459dac929f777e9b9349
Source dataset
uspto-grants-1989_11
Patent number
US04879295

Reaction notes

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