2-Amino-3-methylpyridine → HCID 20145040, compound

HRID 1905997Notes

Reaction equation

HRID 1905997 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12](=O)[CH2:13]Br)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[NH2:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=1>COCCOC>[NH2:1][C:2]1[S:3][C:4]([C:12]2[N:16]=[C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]3[CH:13]=2)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

Participants

4

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 20145096Ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate

Product 1

HCID 20145040HCID 20145040, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate (2.93 g) and 2-amino-3-methyl-pyridine (3.24 g) in 1,2-dimethoxyethane (100 ml) was refluxed for 3 hours. The resulting mixture was evaporated in vacuo. To the residue was added water and ethyl acetate, and the resulting mixture was acidified to pH 0.5 with conc. hydrochloric acid. The separated aqueous layer was adjusted to pH 7.0 with 20% aqueous potassium carbonate and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 2-(2-amino-4-ethoxycarbonyl-5-thiazolyl)-8-methylimidazo[1,2-a]pyridine (2.4 g). mp 243°-245° C. (dec.)

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. additionTo the residue was added water and ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-b7872e0bd2f6474285efb926f251712b
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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