Triethylamine → HCID 18917511, compound

HRID 976411Notes

Reaction equation

HRID 976411 reaction equation
[N:1]1[N:10]2[C:4]([CH2:5][NH:6][C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:41])=[C:27]([CH:40]=1)[C:28]([NH:30][C:31]1[N:36]=[CH:35][C:34]([C:37](Cl)=[O:38])=[CH:33][CH:32]=1)=[O:29]>ClCCl>[N:1]1[N:10]2[C:4]([CH2:5][N:6]([C:37]([C:34]3[CH:33]=[CH:32][C:31]([NH:30][C:28](=[O:29])[C:27]4[CH:40]=[C:23]([F:22])[CH:24]=[CH:25][C:26]=4[CH3:41])=[N:36][CH:35]=3)=[O:38])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 130628255,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepineHCID 155082506-(5-Fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chloride2×

Product 1

HCID 18917511HCID 18917511, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (0° C.) solution of 0.37 g of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine and 836 microliters of triethylamine in 5 ml of dichloromethane is added 0.761 g of 6-[(5-fluoro-2-methylbenzoyl)amino]pyridine-3-carbonyl chloride. The mixture is stirred at room temperature under argon for 5 hours. An additional 420 microliters of triethylamine and 0.38 g of 6-[(5-fluoro-2-methylbenzoyl)amino]pyridine-3-carbonyl chloride is added and the mixture stirred 16 hours. The mixture is diluted with 60 ml of dichloromethane and washed with 25 ml each of H2O, 1M NaHCO3, brine and dried (Na2SO4). The solution is filtered (twice) through a thin pad of hydrous magnesium silicate and the pad washed with dichloromethane. The filtrate is concentrated to give a yellow glass (0.68 g) which is crystallized from ethyl acetate to give 0.38 g of white crystals, m.p. 250°-260° C.; mass spectrum (FABL) 442.4 (M+H).

Workup

  1. stirringthe mixture stirred 16 hours
  2. washwashed with 25 ml each of H2O, 1M NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered (twice) through a thin pad of hydrous magnesium silicate
  5. washthe pad washed with dichloromethane
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-d88e487438fe4b4894b08558a6aaccf8
Source dataset
uspto-grants-1997_03
Patent number
US05612334

Reaction notes

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