Piperidine → 4-(4-Ethyl-piperazin-1-ylmethyl)-N-{3-[2-oxo-3-(1H-pyrrol-2-ylmethylene)-2,3-dihydro-1H-indol-6-ylamino]-phenyl}-3-trifluoromethyl-benzamide

HRID 422031Notes

Reaction equation

[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:35]=[CH:34][C:13]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24]4[CH:32]=[C:31]5[C:27]([CH2:28][C:29](=[O:33])[NH:30]5)=[CH:26][CH:25]=4)[CH:18]=3)=[O:15])=[CH:12][C:11]=2[C:36]([F:39])([F:38])[F:37])[CH2:5][CH2:4]1)[CH3:2].[NH:40]1[CH:44]=[CH:43][CH:42]=[C:41]1[CH:45]=O.N1CCCCC1>CCO>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:35]=[CH:34][C:13]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24]4[CH:32]=[C:31]5[C:27]([C:28](=[CH:45][C:41]6[NH:40][CH:44]=[CH:43][CH:42]=6)[C:29](=[O:33])[NH:30]5)=[CH:26][CH:25]=4)[CH:18]=3)=[O:15])=[CH:12][C:11]=2[C:36]([F:38])([F:39])[F:37])[CH2:5][CH2:4]1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 4-(4-ethyl-piperazin-1-ylmethyl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-6-ylamino)-phenyl]-3-trifluoromethyl-benzamide (200 mg, 0.372 mmol) in EtOH (10 mL) are added pyrrole-2-carboxaldehyde (42 mg, 0.446 mmol) and piperidine (74 μL, 0.74 mmol). The mixture is heated at 80° C. for 2 hours. All the solvent is evaporated to dryness. The crude is recrystallized in EtOH to give 136 mg of the desired compound: 1H NMR (400 MHz, DMSO) δ 10.74 (s, 1 H), 10.34 (s, 1 H), 8.37 (s, 1 H), 8.18-8.24 (m, 2 H), 7.92 (d, 1 H); 7.67 (s, 1 H), 7.46-7.50 (t, 2 H), 7.24-7.28 (m, 3 H), 6.84 (d, 1 H), 6.76 (s, 1 H), 6.72 (m, 1 H), 6.67 (d, 1 H), 6.29-6.31 (m, 1 H), 3.69 (s, 2 H), 3.30 (s, 2 H), 2.30-2.48 (m, 8H), 1.00 (t, 3H); LC-MS: 615.3 (MH+).

Workup

customAll the solvent is evaporated to dryness
customThe crude is recrystallized in EtOH

Sources & evidence

ORD record: ord-7ef9ee490cc34efc84d54b05b3397497
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101608B2

Reaction notes

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