Dimethylformamide → HCID 46830918, compound

HRID 1848339Notes

Reaction equation

HRID 1848339 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]3[N:15]=[C:16]([C:18]4([C:21]([OH:23])=O)[CH2:20][CH2:19]4)[N:17]=[C:13]3[C:12]([O:24][CH3:25])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].C(Cl)(=O)C(Cl)=O.C[N:33](C=O)C>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]3[N:15]=[C:16]([C:18]4([C:21]([NH2:33])=[O:23])[CH2:20][CH2:19]4)[N:17]=[C:13]3[C:12]([O:24][CH3:25])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chloride2×HCID 46830634HCID 46830634, compound

Product 1

HCID 46830918HCID 46830918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[5-(4-Cyano-phenyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-cyclopropanecarboxylic acid (27 mg, 0.08 mmol) was dissolved in DCM (0.3 mL). Oxalyl chloride (0.008 mL, 0.09 mmol) and drop of DMF was added. Stirring for 5 min. Oxalyl chloride (0.003 mL) was added. After 20 min the suspension was concentrated and re-suspended in dioxan (0.3 mL). Aq. NH3 (25%, 0.1 mL) was added. The suspension was stirred at rt for 2 h after which it was concentrated in vacuo. The crude product was mixed with aq. Na2CO3 and the aqueous phase was extracted with DCM (×3). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The title compound was obtained as a slightly coloured solid.

Workup

  1. concentrationAfter 20 min the suspension was concentrated
  2. additionAq. NH3 (25%, 0.1 mL) was added
  3. stirringThe suspension was stirred at rt for 2 h after which it
  4. concentrationwas concentrated in vacuo
  5. additionThe crude product was mixed with aq. Na2CO3
  6. extractionthe aqueous phase was extracted with DCM (×3)
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a00fdd550f6a4a2bac81579bc3c0978e
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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