N,N-dimethylformamide N,N-dimethylacetamide → HCID 178517160, compound

HRID 1645283Notes

Reaction equation

HRID 1645283 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[O:17][C:16]([C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21]([NH2:23])=O)=[CH:15][CH:14]=1.C[N:28]([CH:30]=O)C.CC([N:35](C)C)=O>>[N:28]1[N:35]=[C:21]([C:20]2[CH:19]=[C:18]([C:16]3[O:17][C:13]([CH:12]=[C:5]4[C:4]5[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=5)[NH:7][C:6]4=[O:11])=[CH:14][CH:15]=3)[CH:26]=[CH:25][CH:24]=2)[NH:23][CH:30]=1

Participants

3

Reactant 2

HCID 22628260N,N-dimethylformamide N,N-dimethylacetamideHCID 66774186HCID 66774186, compound

Product 1

HCID 178517160HCID 178517160, compound

Procedure

3-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)benzamide (100 mg, 0.275 mmol) in 5 mL DMF/DMA was stirred at 80° C. during 2 hr. DMF was evaporated and AcOH (10 mL) added. Hydrazine (1 mL) was added dropwise, the mixture was stirred during 10 minutes at R.T., then 45 minutes at 80° C. Water was added and the solid formed isolated by filtration and dried under vacuum. The product was purified by preparative TLC (DCM/MeOH 1%). LCMS (M+1)=389.

Workup

  1. customDMF was evaporated
  2. additionAcOH (10 mL) added
  3. additionHydrazine (1 mL) was added dropwise
  4. custom45 minutes
  5. customat 80° C
  6. additionWater was added
  7. customthe solid formed
  8. customisolated by filtration
  9. customdried under vacuum
  10. customThe product was purified by preparative TLC (DCM/MeOH 1%)

Sources & evidence

ORD record
ord-0edfb442cf5c4a75ac5554fc0c8c5b13
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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