Hydrochloric Acid → HCID 42633066, compound

HRID 2388213Notes

Reaction equation

HRID 2388213 reaction equation
[C:1]([C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[N:10][O:11][C:7]=2[C:6]([OH:19])=[C:5]([C:20](OCC)=[O:21])[N:4]=1)#[N:2].[NH2:25][CH2:26][C:27]([OH:29])=[O:28].C[O-].[Na+].Cl>>[C:1]([C:3]1[C:8]2[C:9]([C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)=[N:10][O:11][C:7]=2[C:6]([OH:19])=[C:5]([C:20]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:21])[N:4]=1)#[N:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 10942334Sodium MethoxideHCID 67529046HCID 67529046, compound

Product 1

HCID 42633066HCID 42633066, compoundYield 66.3%

Procedure

Ethyl 4-cyano-3-(4-fluorophenyl)-7-hydroxyisoxazolo[4,5-c]pyridine-6-carboxylate (101 mg, 0.309 mmol) and glycine (468 mg, 6.18 mmol) were added to sodium methoxide solution (9.3 mL, 4.63 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 73 mg of the title compound. MS: (−) m/z 355.31 (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-224a91bdd3cb4107af26827c4ca40b6d
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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