4-(4-Methylpiperazin-1-yl)aniline → HCID 178434043, compound

HRID 2352908Notes

Reaction equation

O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[C:24]([CH3:30])=[N:25][N:26]([CH3:29])[C:27]=4[Cl:28])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:31].[CH3:32][N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=2)[CH2:35][CH2:34]1>C1COCC1>[CH3:32][N:33]1[CH2:34][CH2:35][N:36]([C:39]2[CH:44]=[CH:43][C:42]([NH:45][CH:2]=[C:3]3[C:11]4[C:6](=[CH:7][C:8]([C:12]([C:14]5[CH:15]=[C:16]([NH:20][C:21]([C:23]6[C:24]([CH3:30])=[N:25][N:26]([CH3:29])[C:27]=6[Cl:28])=[O:22])[CH:17]=[CH:18][CH:19]=5)=[O:13])=[CH:9][CH:10]=4)[NH:5][C:4]3=[O:31])=[CH:41][CH:40]=2)[CH2:37][CH2:38]1

Participants

Conditions

Temperature: 65 °C

Procedure

A small screw cap test tube was charged with 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (prepared below, 100 mg, 0.244 mmol) and THF (2 mL). To the resulting solution was added 4-(4-Methyl-piperazin-1-yl)-phenylamine (46.7 mg, 0.244 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature and concentrated in vacuo. The crude mixture was redissolved into ˜2 mL of EtOAc and then Hexanes were added to causing a precipitate to form. The precipitate was then filtered yielding 45% (0.067 g, 0.109 mmol) of the title compound.

Workup

customA small screw cap test tube
temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
dissolutionThe crude mixture was redissolved into ˜2 mL of EtOAc
additionHexanes were added
customto form
filtrationThe precipitate was then filtered

Sources & evidence

ORD record: ord-fc13c68eb79240adbd6505324deba96a
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749530B2

Reaction notes

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