Diethyl Oxalate → HCID 178470307, compound

HRID 2113623Notes

Reaction equation

HRID 2113623 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:15]([NH2:17])=[O:16].NC1N=C(C2C(Cl)=CC=CN=2)C=CC=1C(N)=O.[C:35](OCC)(=O)[C:36]([O:38][CH2:39][CH3:40])=[O:37]>>[CH2:39]([O:38][C:36]([C:35]1[N:17]=[C:15]([OH:16])[C:3]2[CH:4]=[CH:5][C:6]([C:8]3[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=3)=[N:7][C:2]=2[N:1]=1)=[O:37])[CH3:40]

Participants

4

Reactant 3

HCID 7268Diethyl OxalateHCID 23537069HCID 23537069, compoundHCID 69311936HCID 69311936, compound

Product 1

HCID 178470307HCID 178470307, compound

Conditions

Temperature
160 °C

Procedure

Dissolve 6-amino-3′-methyl-[2,2′]bipyridinyl-5-carboxylic acid amide (1.00 g, 4.38 mmol, prepared in a manner analogous to that described above for the preparation of 6-amino-3′-chloro-[2,2′]bipyridinyl-5-carboxylic acid amide) in diethyl oxalate (24 mL) and heat the mixture at 160° C. for 8 hours or until all starting material is gone as indicated by TLC. Pour the hot mixture onto ice and extract with CH2Cl2 (2×100 mL). Dry the combined organic extracts over Na2SO4. Remove the solvent under reduced pressure. Chromatograph the crude product on silica gel eluting first with CH2Cl2 followed by CH2Cl2/MeOH (95:5) to yield the title compound. MS 311.12 (M+1).

Workup

  1. customprepared in a manner analogous to
  2. additionPour the hot mixture onto ice
  3. extractionextract with CH2Cl2 (2×100 mL)
  4. dry with materialDry the combined organic extracts over Na2SO4
  5. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-5906faaa067647ab9189a17a1a0d5cfc
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

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