Piperidine → HCID 59077606, compound

HRID 1359879Notes

Reaction equation

HRID 1359879 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH2:16]2)(=[O:12])=[O:11].[CH3:23][C:24]1[C:28]([CH2:29][CH2:30][C:31]([N:33]2[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)=[O:32])=[C:27]([CH3:40])[NH:26][C:25]=1[CH:41]=O.N1CCCCC1>C(O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:41]\[C:25]1[NH:26][C:27]([CH3:40])=[C:28]([CH2:29][CH2:30][C:31]([N:33]2[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38]2)=[O:32])[C:24]=1[CH3:23])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 181797685-(2,6-Dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-oneHCID 22561769HCID 22561769, compound

Product 1

HCID 59077606HCID 59077606, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(2,6-Dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one (122 mg, 0.34 mmol), 3,5-dimethyl-4-[3-(4-methyl-piperazin-1-yl)-3-oxo-propyl]-1H-pyrrole-2-carbaldehyde (1.4 eq.) and piperidine (0.5 eq.) in ethanol (2 mL) was stirred at rt for 72 hours. The reaction was concentrated and purified on a silica gel column to give the titled compound as a dark orange brown solid. 1HNMR (400 MHz, DMSO-d6) δ 13.44 (s, 1H, NH), 11.25 (s, 1H, NH), 8.18 (d, 1H), 7.75 (s, 11H), 7.48 (s, 1H), 7.46 (s, 1H), 7.38 (m, 2H), 6.99 (d, J=8 Hz, 1H), 4.85 (s, 2H), 3.3-3.42 (m, 2H), 2.62 (m, 2H), 2.44 (m, 2H), 2.30 (s, 3H, CH3), 2.28 (s, 3H, CH3), 2.1-2.2 (m, 4H), 2.11 (s, 3H, CH3). MS m/z 613 [M−1].

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified on a silica gel column

Sources & evidence

ORD record
ord-bd28a07e9e19411480fb0a8c4dfc1591
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

Loading…