Glycine → HCID 11695634, compound

HRID 2368709Notes

Reaction equation

HRID 2368709 reaction equation
C(O[C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:16]=[C:15]([Br:17])[S:14][C:11]2=[CH:12][N:13]=1)=[O:7])CCC.[NH2:19][CH2:20][C:21]([OH:23])=[O:22]>C[O-].[Na+].CO>[Br:17][C:15]1[S:14][C:11]2=[CH:12][N:13]=[C:8]([C:6]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:7])[C:9]([OH:18])=[C:10]2[CH:16]=1

Participants

5

Reactant 2

HCID 750GlycineHCID 67234000HCID 67234000, compound

Product 1

HCID 11695634HCID 11695634, compoundYield 105.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

2-Bromo-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (7 mg, 0.020 mmol, example 1.g) and glycine (38 mg, 0.5 mmol) were suspended in 1 mL of 0.5 N sodium methoxide in methanol. The resultant mixture was heated to 120° C. for 10 min. using a CEM microwave reactor. The reaction mixture was cooled, concentrated to ca. 0.2 mL under high vacuum, and diluted with 1 mL of 1.0 N HCl. The resultant precipitate was collected on a fine glass filter funnel, washed twice with water, and dried under hi-vacuum to yield 7 mg of the title compound. MS: (−) m/z 328.98, 331.03 (M−1, 79Br/81Br)

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated to ca. 0.2 mL under high vacuum
  3. additiondiluted with 1 mL of 1.0 N HCl
  4. customThe resultant precipitate was collected on a fine glass
  5. filtrationfilter funnel
  6. washwashed twice with water
  7. customdried under hi-vacuum

Sources & evidence

ORD record
ord-a972024842b24a96ba09fb9e41c2f816
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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