N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]-N-{[3-(4-methylpiperazin-1-yl)-2,3,4,5-tetrahydrooxepin-3-yl]methyl}cyclohexanecarboxamide → N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]-N-{[3-(4-methylpiperazin-1-yl)oxepan-3-yl]methyl}cyclohexanecarboxamide

HRID 1943016Notes

Reaction equation

HRID 1943016 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH2:12][N:13]([CH2:22][C:23]2([N:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)[CH2:29][CH2:28][CH:27]=[CH:26][O:25][CH2:24]2)[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[C:3]1=[O:37]>CCO.[Pd]>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH2:12][N:13]([CH2:22][C:23]2([N:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)[CH2:29][CH2:28][CH2:27][CH2:26][O:25][CH2:24]2)[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[C:3]1=[O:37]

Participants

4

Reactant 1

HCID 58415943N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]-N-{[3-(4-methylpiperazin-1-yl)-2,3,4,5-tetrahydrooxepin-3-yl]methyl}cyclohexanecarboxamide

Product 1

HCID 46191770N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]-N-{[3-(4-methylpiperazin-1-yl)oxepan-3-yl]methyl}cyclohexanecarboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]-N-{[3-(4-methylpiperazin-1-yl)-2,3,4,5-tetrahydrooxepin-3-yl]methyl}cyclohexanecarboxamide (59 mg, 0.116 mmole) was hydrogenated at atmospheric pressure (H2 balloon) with 10% Pd/C (13 mg, 0.012 mmole) in EtOH at RT. After 16 hr the mixture was filtered through a pad of Celite washing with EtOH and concentrated to an off-white solid (57 mg, 96%). 1H-NMR (CDCl3, 500 MHz) d 7.58 (t, J=7.08 Hz, 1 H), 7.52 (d, J=6.59 Hz, 1 H), 7.39 (d, J=8.30 Hz, 1 H), 7.25 (m, 1 H), 7.21 (s, 1 H), 5.34 (d, J=19.78 Hz, 1 H), 4.58 (d, J=19.78 Hz, 1 H), 4.31 (d, J=14.41 Hz, 1 H), 4.01 (m, 1 H), 3.88 (dd AB, J=13.91 and 74.95 Hz, 1 H), 3.78 (s, 3 H), 3.37 (m, 1 H), 2.91 (d, J=14.65 Hz, 1 H), 2.80-2.26 (m, 12 H), 1.84-1.06 (m, 17 H). HRMS (M+H)+ calculated 509.3486. found 509.3491.

Workup

  1. filtrationAfter 16 hr the mixture was filtered through a pad of Celite
  2. washwashing with EtOH
  3. concentrationconcentrated to an off-white solid (57 mg, 96%)

Sources & evidence

ORD record
ord-5c55556398724af2a624dab3c56b0900
Source dataset
uspto-grants-2013_03
Patent number
US08389720B2

Reaction notes

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