Triethylamine → HCID 56832686, compound

HRID 920983Notes

Reaction equation

HRID 920983 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16](O)=[O:17])=[N:4][NH:3]1.ON1C2C=CC=CC=2N=N1.[CH3:32][NH:33][C:34]([C:36]1[N:37]=[C:38]([C:45]([F:48])([F:47])[F:46])[N:39]2[CH2:44][CH2:43][NH:42][CH2:41][C:40]=12)=[O:35].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C)C=O>[CH3:32][NH:33][C:34]([C:36]1[N:37]=[C:38]([C:45]([F:48])([F:46])[F:47])[N:39]2[CH2:44][CH2:43][N:42]([C:16](=[O:17])[C:15]3[CH:19]=[CH:20][CH:21]=[C:13]([CH2:12][C:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C:2](=[O:1])[NH:3][N:4]=4)[CH:14]=3)[CH2:41][C:40]=12)=[O:35]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 251319063-((4-Oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acidHCID 68011887HCID 68011887, compound

Product 1

HCID 56832686HCID 56832686, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[(4-Oxo-3H-phthalazin-1-yl)methyl]benzoic acid 15a (186 mg, 0.67 mmol) was dissolved in 20 mL of N,N-dimethylformamide, followed by addition of 1-hydroxybenzotriazole (98 mg, 0.73 mmol), crude N-methyl-3-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxamide 13a (150 mg, 0.61 mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (173 mg, 0.91 mmol) and triethylamine (253 μL, 1.82 mmol). After stirring for 12 hours, the reaction mixture was was concentrated under reduced pressure, added with 50 mL of H2O and extracted with ethyl acetate (50 mL×3). The organic phase was combined, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by thin layer chromatography with elution system A to obtain N-methyl-7-[3-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoyl]-3-(trifluoromethyl)-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-1-carboxamide 21 (280 mg, yield 90.0%) as a light yellow solid.

Workup

  1. concentrationthe reaction mixture was was concentrated under reduced pressure
  2. additionadded with 50 mL of H2O
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by thin layer chromatography with elution system

Sources & evidence

ORD record
ord-b45c1bb97fc049b6830cc2d8fa9db3cf
Source dataset
uspto-grants-2016_03
Patent number
US09273052B2

Reaction notes

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