Formic Acid → 7-sec.Butylamino-5-methylthiazolo[5,4-b]pyridine-6-carboxylic acid, ethyl ester

HRID 1606542Notes

Reaction equation

HRID 1606542 reaction equation
[NH2:1][C:2]1[C:3]([NH:15][CH:16]([CH2:18][CH3:19])[CH3:17])=[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([CH3:9])=[N:6][C:7]=1[SH:8].[CH:20](O)=O>>[CH:16]([NH:15][C:3]1[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([CH3:9])[N:6]=[C:7]2[S:8][CH:20]=[N:1][C:2]=12)([CH2:18][CH3:19])[CH3:17]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 178469256HCID 178469256, compound

Product 1

HCID 1317101617-sec.Butylamino-5-methylthiazolo[5,4-b]pyridine-6-carboxylic acid, ethyl ester

Procedure

2.8 g. of 5-amino-4-sec.butylamino-6-mercapto-2-methylpyridine-3-carboxylic acid, ethyl ester are refluxed in 10 ml. of formic acid for 12 hours. After this time, the excess acid is removed in vacuo and the residue is dissolved in 10 ml. of water. The aqueous solution is made alkaline with sodium hydroxide and extracted twice, each time with 10 ml. of ether. The ether layer is collected, dried over calcium chloride and evaporated to dryness. The residue, 7-sec.butylamino-5-methylthiazolo[5,4-b]pyridine-6-carboxylic acid, ethyl ester is distilled in vacuo, b. p.0.01 180°-185°, yield 1.8 g. (62%).

Workup

  1. customAfter this time, the excess acid is removed in vacuo
  2. dissolutionthe residue is dissolved in 10 ml
  3. extractionextracted twice
  4. customThe ether layer is collected
  5. dry with materialdried over calcium chloride
  6. customevaporated to dryness
  7. distillationThe residue, 7-sec.butylamino-5-methylthiazolo[5,4-b]pyridine-6-carboxylic acid, ethyl ester is distilled in vacuo, b
  8. customp.0.01 180°-185°, yield 1.8 g

Sources & evidence

ORD record
ord-a7f7e2fe2a4d46088c97e6cf0ae9278b
Source dataset
uspto-grants-1976_04
Patent number
US03953461

Reaction notes

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