HCID 68453809, compound → HCID 11848246, compound

HRID 2357590Notes

Reaction equation

HRID 2357590 reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([C:23]3[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH:28]=3)=[N:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.[H][H]>[Pd].C(OCC)(=O)C>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([CH:23]3[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]3)=[N:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 68453809HCID 68453809, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11848246HCID 11848246, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-cyclopropyl-4-methyl-3-(1-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phthalazin-6-yl)benzamide (20 mg, 50 μmol), 20 mg 10% palladium on activated carbon in 20 mL ethyl acetate was stirred under 50 psi hydrogen at 22° C. After 2 h reaction, the reaction was monitored for product (MS=401) and starting material (MS=399). The reaction mixture was stirred under 50 psi hydrogen at 22° C. for another 2 h, MS showed all starting material was converted to product. The mixture was filtered and washed with methanol 50 mL. After concentrating the filtrate, the residue was purified by PTLC to obtain the title compound (10 mg) as a pale yellow solid. Found MS (ES+): 401 (M+H)+.

Workup

  1. customAfter 2 h reaction
  2. filtrationThe mixture was filtered
  3. washwashed with methanol 50 mL
  4. concentrationAfter concentrating the filtrate
  5. customthe residue was purified by PTLC

Sources & evidence

ORD record
ord-3e827c02103446c3b45b9f6a4c3c08e6
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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