Hydrochloric Acid → HCID 42633065, compound

HRID 2388211Notes

Reaction equation

HRID 2388211 reaction equation
[C:1]([C:3]1[C:8]2[C:9]([C:12]3[S:13][CH:14]=[CH:15][CH:16]=3)=[N:10][O:11][C:7]=2[C:6]([OH:17])=[C:5]([C:18]([O:20]CC)=O)[N:4]=1)#[N:2].[NH2:23][CH2:24][C:25]([OH:27])=[O:26].C[O-].[Na+].Cl>>[C:1]([C:3]1[C:8]2[C:9]([C:12]3[S:13][CH:14]=[CH:15][CH:16]=3)=[N:10][O:11][C:7]=2[C:6]([OH:17])=[C:5]([C:18]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:20])[N:4]=1)#[N:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 10942334Sodium MethoxideHCID 67530164HCID 67530164, compound

Product 1

HCID 42633065HCID 42633065, compoundYield 67.9%

Procedure

Ethyl 4-cyano-7-hydroxy-3-(thiophen-2-yl)isoxazolo[4,5-c]pyridine-6-carboxylate (136 mg, 0.432 mmol) and glycine (648 mg, 8.63 mmol) were added to sodium methoxide solution (13 mL, 6.48 mmol, 0.5 M in MeOH) and the mixture was refluxed for 3 days. The mixture was cooled to room temperature and 0.25 M hydrochloric acid was added until pH was 3. The precipitate was isolated by filtration and dried under vacuum to give 101 mg of the title compound. MS: (−) m/z 343.28 (M−1).

Workup

  1. temperaturethe mixture was refluxed for 3 days
  2. customThe precipitate was isolated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-aa933d2acc4c49fb995f6e7e73dcf586
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

Loading…