HCID 21106536, compound → HCID 178495849, compound

HRID 1765363Notes

Reaction equation

HRID 1765363 reaction equation
C([N:5]1[C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[N:13]([CH2:22][CH2:23][O:24][CH3:25])[N:12]=2)=[CH:8][C:7]([CH3:26])=[N:6]1)(C)(C)C>C(O)=O.O>[CH3:25][O:24][CH2:23][CH2:22][N:13]1[N:12]=[C:11]([NH:10][C:9]2[NH:5][N:6]=[C:7]([CH3:26])[CH:8]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:21]

Participants

4

Reactant 1

HCID 21106536HCID 21106536, compound

Product 1

HCID 178495849HCID 178495849, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

4-(2-tert-Butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(2-methoxy-ethyl)-2H-phthalazin-1-one (0.36 g, 1.0 mmol) was dissolved in formic acid (20 ml) and heated at reflux for 4 h. The resulting raw product was dissolved in H2O and dichloromethane, after evaporation of formic acid. Addition of NaHCO3 resulted in precipitation of a solid, which was collected by filtration. Subsequent washing with H2O, dichloromethane and diethyl ether and drying in vacuum at 40° C. yielded the desired product 2-(2-Methoxyethyl)-4-(5-methyl-2H-pyrazol-3-ylamino)-2H-phthalazin-1-one (example O-1) (0.28 g, 94%). 1H-NMR: (400 MHz, D6-DMSO) 9.21 (1H, s), 8.43 (1H, d), 8.29 (1H, d), 8.14 (1H, s), 7.84–7.94 (2H, m), 6.28 (1H, s), 4.23 (2H, t), 3.73 (2H, t), 3.33 (3H, s), 2.23 (3H, s); MS (ESI+)=300.3 (M+H)+

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. customdichloromethane, after evaporation of formic acid
  4. additionAddition of NaHCO3
  5. customresulted in precipitation of a solid, which
  6. filtrationwas collected by filtration
  7. washSubsequent washing with H2O, dichloromethane and diethyl ether
  8. customdrying in vacuum at 40° C.

Sources & evidence

ORD record
ord-537dea28857a47d7a639a803e968c0fc
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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