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

HRID 74650Notes

Reaction equation

HRID 74650 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](=[CH:34][C:35]([F:39])=[CH:36][CH:37]=3)[CH2:32][CH2:31]2)=[O:29])[CH:25]=[C:24]([O:40][CH3:41])[N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[F:39][C:35]1[CH:34]=[C:33]2[C:38](=[CH:37][CH:36]=1)[N:30]([C:28]([C:26]1[CH:25]=[C:24]([O:40][CH3:41])[N:23]=[C:22]([N:17]3[CH2:18][CH2:19][CH:14]([N:10]4[CH2:9][CH2:8][C:7]5[CH:20]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=5[NH:12][C:11]4=[O:13])[CH2:15][CH2:16]3)[CH:27]=1)=[O:29])[CH2:31][CH2:32]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 58386441(2-Chloro-6-methoxypyridin-4-yl)-(5-fluoro-2,3-dihydroindol-1-yl)-methanone

Product 1

HCID 426138053-[4'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-6'-methoxy-3,4,5,6-tetrahydro-2H-[1,2']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

633 mg (2.3 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 700 mg (2.28 mmol) (2-chloro-6-methoxy-pyridin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone and 953.6 mg (6.9 mmol) potassium carbonate were stirred in 5 mL of NMP for 8 h at 130° C. The undissolved solid was filtered off and the filtrate was purified by HPLC. The product-containing fractions were combined and concentrated to dryness by rotary evaporation. For further purification the residue was combined with DMF and the undissolved solid was suction filtered and dried.

Workup

  1. filtrationThe undissolved solid was filtered off
  2. customthe filtrate was purified by HPLC
  3. concentrationconcentrated to dryness by rotary evaporation
  4. customFor further purification the residue
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-a056b08e0f4744fc9765f3a702a69306
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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