Triethylamine → N-[5-(4H-Pyrazolo[5,1-c][1,4]benzodiazepin-5(10H)-ylcarbonyl)-2-pyridinyl]-[1,1'-biphenyl]-2-carboxamide

HRID 976412Notes

Reaction equation

HRID 976412 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.[C:22]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:23]([C:28]([NH:30][C:31]2[N:36]=[CH:35][C:34]([C:37](Cl)=[O:38])=[CH:33][CH:32]=2)=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=1>ClCCl.O>[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]([C:23]4[C:22]([C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:29])=[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

6

Reactant 3

HCID 8471TriethylamineHCID 130628255,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepineHCID 220997926-[([1,1'-Biphenyl]-2-ylcarbonyl)amino]-3-pyridinecarbonyl chloride

Product 1

HCID 21462557N-[5-(4H-Pyrazolo[5,1-c][1,4]benzodiazepin-5(10H)-ylcarbonyl)-2-pyridinyl]-[1,1'-biphenyl]-2-carboxamideYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a chilled (0° C.) solution of 0.185 g of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine and 417 μl of triethylamine in 3.5 ml of dichloromethane is added 0.35 g of 6-(2-biphenylcarbonyl)aminopyridine-3-carbonyl chloride in 1.5 ml of dichloromethane. The mixture is stirred at room temperature under argon for hours, diluted with 40 ml of dichloromethane and 20 ml of water. The organic layer is separated, washed with 20 ml of brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate. The filtrate is concentrated to dryness under vacuum to give 0.4 g of solid. The solid is purified on silica gel prep-plates with ethyl acetate-hexane (3:1) as eluent to give 170 mg of a brown glass, m.p. 110°-150° C.

Workup

  1. customThe organic layer is separated
  2. washwashed with 20 ml of brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. concentrationThe filtrate is concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-8edc34009a4b4984b202c7d0915742fb
Source dataset
uspto-grants-1997_03
Patent number
US05612334

Reaction notes

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