Potassium Carbonate → 3-[4'-(4,5-difluoro-2,3-dihydro-indole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

HRID 74656Notes

Reaction equation

HRID 74656 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=1.Cl[C:22]1[CH:27]=[C:26]([C:28]([N:30]2[C:38]3[C:33](=[C:34]([F:40])[C:35]([F:39])=[CH:36][CH:37]=3)[CH2:32][CH2:31]2)=[O:29])[CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[F:40][C:34]1[C:35]([F:39])=[CH:36][CH:37]=[C:38]2[C:33]=1[CH2:32][CH2:31][N:30]2[C:28]([C:26]1[CH:27]=[CH:22][N:23]=[C:24]([N:17]2[CH2:18][CH2:19][CH:14]([N:10]3[CH2:9][CH2:8][C:7]4[CH:20]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=4[NH:12][C:11]3=[O:13])[CH2:15][CH2:16]2)[CH:25]=1)=[O:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 58117528(2-Chloro-pyridin-4-yl)-(4,5-difluoro-2,3-dihydro-indol-1-yl)-methanone

Product 1

HCID 583865063-[4'-(4,5-difluoro-2,3-dihydro-indole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.18 g (0.67 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 0.020 g (0.68 mmol) (2-chloro-pyridin-4-yl)-(4,5-difluoro-2,3-dihydro-indol-1-yl)-methanone and 97 mg (0.70 mmol) potassium carbonate were stirred in 3 mL NMP for 4 h at 130° C., then overnight at RT. The reaction mixture was purified by HPLC. The product-containing fractions were combined and freeze-dried.

Workup

  1. customovernight
  2. customat RT
  3. customThe reaction mixture was purified by HPLC
  4. customfreeze-dried

Sources & evidence

ORD record
ord-5789d0a2d165401085778e640f12d138
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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