Triethylamine → HCID 68840826, compound

HRID 229729

Reaction equation

HRID 229729 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[NH:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)[CH2:6][C:5]=2[C:4](=O)[CH2:3]1.Cl.[NH2:24][NH2:25].C(N(CC)CC)C>C(O)C>[CH3:1][CH:2]1[CH2:11][C:10]2[N:9]=[N:8][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[CH:6][C:5]=2[C:4](=[N:24][NH2:25])[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115031Hydrazinium chlorideHCID 42467327-Methyl-3-(3-(trifluoromethyl)phenyl)-1,4,6,7,8-pentahydrocinnolin-5-one

Product 1

HCID 68840826HCID 68840826, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol solution (3 mL) of 7-methyl-3-(3-trifluoromethylphenyl)-4,6,7,8-terahydro-1H-cinnolin-5-one (230 mg, 0.74 mmol) obtained in Example 65 were added hydrazine hydrochloride (77.3 mg, 0.74 mmol) and triethylamine (0.206 mL, 1.48 mmol) and stirred at room temperature over night. The reaction liquid was concentrated, followed by purification of residue with silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain an objective compound (29.5 mg, 12.5%).

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated
  3. customfollowed by purification of residue with silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-392929630b374aabaa55e4ad9670f4d9
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Linked notes

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