Potassium Carbonate → 3-[2'-(2,3-dihydroindole-1-carbonyl)-3,4,5,6-tetrahydro-2H-1,4'-bipyridinyl-4-yl]-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

HRID 74622Notes

Reaction equation

HRID 74622 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:25]1[CH2:30][CH2:29][CH:28]([N:31]2[CH2:37][CH2:36][C:35]3[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=3[NH:33][C:32]2=[O:42])[CH2:27][CH2:26]1>C1COCC1>[N:10]1([C:8]([C:4]2[CH:3]=[C:2]([N:25]3[CH2:26][CH2:27][CH:28]([N:31]4[CH2:37][CH2:36][C:35]5[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=5[NH:33][C:32]4=[O:42])[CH2:29][CH2:30]3)[CH:7]=[CH:6][N:5]=2)=[O:9])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 25637566(4-Chloro-pyridin-2-yl)-(2,3-dihydro-indol-1-yl)-methanone

Product 1

HCID 426132183-[2'-(2,3-dihydroindole-1-carbonyl)-3,4,5,6-tetrahydro-2H-1,4'-bipyridinyl-4-yl]-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

110 mg (0.43 mmol) (4-chloro-pyridin-2-yl)-(2,3-dihydro-indol-1-yl)-methanone, 150 mg (1.0 mmol) potassium carbonate and 100 mg (0.41 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one in 10 mL THF were refluxed for 3 days. Then the reaction mixture was evaporated down using the rotary evaporator, taken up in 20 mL xylene and refluxed for a further 3 days. The solid was filtered off and the filtrate evaporated down i. vac. The residue was dissolved in DMF and purified by preparative HPLC. The product fractions were combined and lyophilised.

Workup

  1. customThen the reaction mixture was evaporated down
  2. customthe rotary evaporator
  3. temperaturerefluxed for a further 3 days
  4. filtrationThe solid was filtered off
  5. customthe filtrate evaporated down i
  6. dissolutionThe residue was dissolved in DMF
  7. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-a713b8b762d3463ca804602f6597b9ec
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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