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Tetrahydrofuran → HCID 178456637, compound

HRID 641021
Notes
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Reaction equation

HRID 641021 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]([CH:28]([CH3:30])[CH3:29])[N:25]=[CH:26][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:31].C1COCC1.[CH3:37][N:38]1[CH2:43][CH2:42][N:41]([C:44]2[CH:49]=[CH:48][C:47]([NH2:50])=[CH:46][CH:45]=2)[CH2:40][CH2:39]1>CCOC(C)=O.CCCCCC>[CH3:37][N:38]1[CH2:39][CH2:40][N:41]([C:44]2[CH:49]=[CH:48][C:47]([NH:50][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]([CH:28]([CH3:29])[CH3:30])[N:25]=[CH:26][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:31])=[CH:46][CH:45]=2)[CH2:42][CH2:43]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 178456638HCID 178456638, compound

Product 1

HCID 178456637HCID 178456637, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2-Isopropyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (prepared below, 138 mg, 0.3314 mmol) and THF (3.3 mL). To the resulting solution was added 4-(4-methyl-piperazin-1-yl)-phenylamine (63.3 mg, 0.331 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 65% yield (0.127 g, 0.215 mmol).

Workup

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

Sources & evidence

ORD record
ord-e06cf4d7ef524f0fbe2f5f7693bb5d6c
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07692005B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes