Glycine → HCID 68428236, compound

HRID 642408Notes

Reaction equation

HRID 642408 reaction equation
C(O[C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:16]([Cl:17])=[C:15]([Cl:18])[N:14]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])C.[NH2:25][CH2:26][C:27]([OH:29])=[O:28]>C[O-].[Na+].CO>[Cl:18][C:15]1[N:14]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[C:9]2=[C:10]([C:12]#[N:13])[N:11]=[C:6]([C:4]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:5])[C:7]([OH:24])=[C:8]2[C:16]=1[Cl:17]

Participants

5

Reactant 2

HCID 750GlycineHCID 68428125HCID 68428125, compound

Product 1

HCID 68428236HCID 68428236, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

7-Cyano-2,3-dichloro-4-hydroxy-1-(3-methyl-butyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (80 mg, 0.22 mmol) and glycine (324 mg, 4.32 mmol) were suspended in 8.64 mL of 0.5 N sodium methoxide in methanol. The reaction was heated at reflux temperature overnight, cooled, and concentrated. The residue was dissolved in water (15 mL), and the solution was acidified to pH 1-2 with 1 N hydrochloric acid. The title compound (60 mg) was collected by filtration as a light yellow solid. MS: (+) m/z 399.2 (M+1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux temperature overnight
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in water (15 mL)
  6. filtrationThe title compound (60 mg) was collected by filtration as a light yellow solid

Sources & evidence

ORD record
ord-567a198dfd984b9e8ffc7738c52a5373
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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