Methanol → Methyl 3-[5-(2-aminopyridin-4-yl)-2-ethyl-1,3-thiazol-4-yl]benzoate

HRID 1727373Notes

Reaction equation

HRID 1727373 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH:8]2[S:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]2([C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26]([OH:28])=[O:27])C2C=CC=C(C#N)C=2)[CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:39]O>>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]=2[C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26]([O:28][CH3:39])=[O:27])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 68830741HCID 68830741, compound

Product 1

HCID 22932716Methyl 3-[5-(2-aminopyridin-4-yl)-2-ethyl-1,3-thiazol-4-yl]benzoateYield 85%

Conditions

Temperature
70 °C

Procedure

To a solution of 3-[5-(2-amino-4-pyridyl)-4-(3-cyanophenyl)-2-ethyl-1,3-thiazol-4-yl]benzoic acid (0.3 g, 1.0 mmol) in methanol (10 mL) was added concentrated sulfuric acid (0.1 mL) and the mixture was stirred for 5 hours at 70° C. The reaction mixture was basified with sodium hydroxide solution and extracted with ethyl acetate. The extracts were washed with water, then, dried and concentrated. The residue was washed with hexane-ethyl acetate to obtain a title compound (0.29 g, yield 85%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. washThe residue was washed with hexane-ethyl acetate

Sources & evidence

ORD record
ord-a4ad2a70b3514c82bb7f5da2967d16f7
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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