Pyrrole-2-carboxaldehyde → HCID 66674929, compound

HRID 422022Notes

Reaction equation

HRID 422022 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:34]=[CH:33][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]4[CH:24]=[CH:25][CH:26]=[C:27]5[C:31]=4[NH:30][C:29](=[O:32])[CH2:28]5)[CH:17]=3)=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[NH:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[CH:40]=O>C(O)C.N1CCCCC1>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]4[CH:24]=[CH:25][CH:26]=[C:27]5[C:31]=4[NH:30][C:29](=[O:32])[C:28]5=[CH:40][C:36]4[NH:35][CH:39]=[CH:38][CH:37]=4)[CH:17]=3)=[O:14])=[CH:33][CH:34]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 598043654-(4-methyl-piperazin-1-ylmethyl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-7-ylamino)-phenyl]-benzamide

Product 1

HCID 66674929HCID 66674929, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(4-methyl-piperazin-1-ylmethyl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-7-ylamino)-phenyl]-benzamide (23 mg, 0.05 mmol) is heated with 1H-pyrrole-2-carbaldehyde (5 mg, 0.05 mmol) in ethanol (2 ml) in the presence of 2 drops of piperidine for 12 hours. It is then concentrated and purified by HPLC to give the desired compound: 1H NMR (DMSO-d6) δ 2.40-2.48 (m, 2H), 2.79 (s, 3H), 2.96-3.08 (m, 4H), 3.36-3.46 (m, 2H), 3.75 (s, 2H), 6.37 (s, 1H), 6.71 (d, 1H, J=7.8 Hz), 6.85 (s, 1H), 6.97 (t, 1H, J=7.8 Hz), 7.11 (d, 1H, J=7.2 Hz), 7.19 (t, 1H, J=7.8 Hz), 7.24 (d, 1H, J=7.8 Hz), 7.30 (t, 1H, J=7.8 Hz), 7.36 (s, 1H), 7.47 (d, 2H, J=7.8 Hz), 7.53 (s, 1H), 7.75 (s, 1H), 7.93 (d, 2H, J=7.8 Hz), 10.13 (s, 1H), 10.60 (s, 1H), 13.36 (s, 1H); LC-MS: 533.2 (MH+).

Workup

  1. concentrationIt is then concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-ffc245447bd44822b4a1ad4b70809ea7
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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