HCID 21106538, compound → HCID 178428371, compound

HRID 1783690Notes

Reaction equation

HRID 1783690 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]([C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:24][CH:23]=3)[N:12]=2)=[CH:8][C:7]([CH3:34])=[N:6]1)(C)(C)C>C(O)=O.C(Cl)Cl>[CH3:34][C:7]1[CH:8]=[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]([C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:24][CH:23]=3)[N:12]=2)[NH:5][N:6]=1

Participants

4

Reactant 1

HCID 21106538HCID 21106538, compound

Product 1

HCID 178428371HCID 178428371, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
95 °C

Procedure

4-(2-tert-Butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-piperidin-1-yl-phenyl)-2H-phthalazin-1-one (0.012 g, 0.026 mmol) was dissolved in formic acid (1 ml) and heated at 95° C. for 4 h. The resulting raw product was dissolved in DCM, after evaporation of formic acid. Extraction with a saturated aqueous NaHCO3 solution, combining of the organic phases, evaporation of the solvent in vacuum and purification by chromatography over silica gel with DCM:MeOH (20:1) yielded the title compound (0.006 g, 57%). 1H-NMR: (400 MHz, D6-DMSO) 11.81 (1H, s), 9.21 (1H, s), 8.48 (1H, d), 8.35 (1H, d), 7.87-7.96 (2H, m), 7.50 (2H, d), 7.01 (2H, d), 6.25 (1H, s), 3.21 (4H, m), 2.19 (3H, s), 1.64 (4H, m), 1.60 (2H, m); MS (ESI+)=401.29 (M+H)+.

Workup

  1. customafter evaporation of formic acid
  2. extractionExtraction with a saturated aqueous NaHCO3 solution
  3. customcombining of the organic phases, evaporation of the solvent in vacuum and purification by chromatography over silica gel with DCM:MeOH (20:1)

Sources & evidence

ORD record
ord-c11b2e091a434ce3a5ac087e934763d8
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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