Tetrahydrofuran → HCID 178480712, compound

HRID 2352951Notes

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[N:24]([CH3:32])[N:25]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:33].C1COCC1.[CH3:39][N:40]1[CH2:45][CH2:44][N:43]([C:46]2[CH:51]=[CH:50][C:49]([NH2:52])=[CH:48][CH:47]=2)[CH2:42][CH2:41]1>CCOC(C)=O.CCCCCC>[CH3:39][N:40]1[CH2:41][CH2:42][N:43]([C:46]2[CH:51]=[CH:50][C:49]([NH:52][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[N:24]([CH3:32])[N:25]=[C:26]([C:28]([CH3:30])([CH3:29])[CH3:31])[CH:27]=6)=[O:22])[CH:17]=[CH:18][CH:19]=5)=[O:13])=[CH:9][CH:10]=4)[NH:5][C:4]3=[O:33])=[CH:48][CH:47]=2)[CH2:44][CH2:45]1

Participants

Conditions

Temperature: 65 °C

Procedure

A small screw cap test tube was charged with 5-tert-Butyl-2-methyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (prepared below, 128 mg, 0.288 mmol) and THF (3.0 mL). To the resulting solution was added 4-(4-methyl-piperazin-1-yl)-phenylamine (54.8 mg, 0.286 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and diluted with EtOAc (˜5 mL) and Hexane (˜40 mL). The precipitate that formed was collected by filtration and washed with 0° C. iPrOH (˜10 mL) to afford the title compound in 29% yield (0.051 g, 0.083 mmol).

Workup

customA small screw cap test tube
temperatureSubsequently, the reaction mixture was cooled to room temperature
customThe precipitate that formed
filtrationwas collected by filtration
washwashed with 0° C. iPrOH (˜10 mL)

Sources & evidence

ORD record: ord-85b546342d8f4561bc369f44545a5359
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749530B2

Reaction notes

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