Methylamine → HCID 56832572, compound

HRID 920962Notes

Reaction equation

HRID 920962 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:33]([F:36])([F:35])[F:34])[N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]([CH2:21][C:22]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:25](=[O:32])[NH:24][N:23]=4)[CH:17]=[CH:18][C:19]=3[F:20])=[O:13])[CH2:8][C:7]=12.[CH3:37][NH2:38].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O1CCCC1>[F:20][C:19]1[CH:18]=[CH:17][C:16]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25](=[O:32])[NH:24][N:23]=2)=[CH:15][C:14]=1[C:12]([N:9]1[CH2:10][CH2:11][N:6]2[C:5]([C:33]([F:36])([F:34])[F:35])=[N:4][C:3]([CH2:2][NH:38][CH3:37])=[C:7]2[CH2:8]1)=[O:13]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 68011885HCID 68011885, compound

Product 1

HCID 56832572HCID 56832572, compoundYield 10.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[[3-[1-(Chloromethyl)-3-(trifluoromethyl)-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carbonyl]-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 9a (372 mg, 1.25 mmol) was dissolved in 5 mL of acetonitrile, followed by addition of 0.6 mL of a 2 M solution of methylamine in tetrahydrofuran and potassium carbonate (159 mg, 1.15 mmol). The reaction mixture was heated to reflux for 6 hours. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure and was purified by thin layer chromatography with elution system A to obtain 4-[[4-fluoro-3-[1-(methylaminomethyl)-3-(trifluoromethyl)-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carbonyl]phenyl]methyl]-2H-phthalazin-1-one 9 (20 mg, yield 10.1%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customwas purified by thin layer chromatography with elution system

Sources & evidence

ORD record
ord-0b920adf8fd747deb28193f603a5514c
Source dataset
uspto-grants-2016_03
Patent number
US09273052B2

Reaction notes

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