Dimethylformamide → HCID 178425826, compound

HRID 251381Notes

Reaction equation

HRID 251381 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27](=O)[NH2:28])[CH:22]=1.COC(OC)[N:34]([CH3:36])C.C[N:40](C=O)C>>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[NH:34][CH:36]=[N:40][N:28]=2)[CH:22]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 11153907HCID 11153907, compound

Product 1

HCID 178425826HCID 178425826, compoundYield 51%

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-[5-amino-4-(3-carbamoyl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide (120 mg) in DMF (2 mL), was added N,N-dimethylformamide dimethyl acetal (5 ml) and the solution was stirred at 80° C. overnight. The solvent was removed, residue was dissolved in AcOH (5 ml), hydrazine monohydrate (3 ml) was added and the mixture stirred at 90° C. overnight. The solution was acidified with hydrochloric acid to pH - land stirred at 80° C. overnight. The solvent was removed and the residue was resuspended in EtOAc, then washed by aqueous K2CO3 solution, water, and brine, and concentrated. The crude product was purified by column chromatography on silica gel eluted with EtOAc to provide product as a white solid (65 mg, 51%). HPLC (4 minute 10-90 gradient) tR 1.58 min; MS m/z 428.18 [M+H]+.

Workup

  1. customThe solvent was removed
  2. dissolutionresidue was dissolved in AcOH (5 ml)
  3. additionhydrazine monohydrate (3 ml) was added
  4. stirringthe mixture stirred at 90° C. overnight
  5. stirringto pH - land stirred at 80° C. overnight
  6. customThe solvent was removed
  7. washwashed by aqueous K2CO3 solution, water, and brine
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography on silica gel
  10. washeluted with EtOAc

Sources & evidence

ORD record
ord-261d76360e3d46eb9cb905fef6a17204
Source dataset
uspto-grants-2011_01
Patent number
US07863314B2

Reaction notes

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