Potassium Carbonate → 3-[6'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-2'-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 74682Notes

Reaction equation

HRID 74682 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])[CH:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]2[NH:32][C:31](=[O:33])[N:30]([CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[CH2:29][CH2:28][C:27]=2[CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[F:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:11]([C:9]([C:4]1[N:5]=[C:6]([CH3:8])[CH:7]=[C:2]([N:37]3[CH2:36][CH2:35][CH:34]([N:30]4[CH2:29][CH2:28][C:27]5[CH:40]=[C:23]([O:22][CH3:21])[CH:24]=[CH:25][C:26]=5[NH:32][C:31]4=[O:33])[CH2:39][CH2:38]3)[CH:3]=1)=[O:10])[CH2:12][CH2:13]2

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 58386723HCID 58386723, compound

Product 1

HCID 426130593-[6'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-2'-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

125 mg (0.43 mmol) (4-chloro-6-methyl-pyridin-2-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone, 118 mg (0.43 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 89 mg (0.65 mmol) potassium carbonate in 2.0 mL NMP were stirred for 10 h at 130° C. Then the reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. customfreeze-dried

Sources & evidence

ORD record
ord-64b68e5cee0f44239a57c62f5c0835a7
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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