Tetrahydrofuran → HCID 178463061, compound

HRID 640839Notes

Reaction equation

HRID 640839 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]4[N:23]([CH2:28][CH3:29])[N:24]=[C:25]([CH3:27])[CH:26]=4)=[O:21])=[CH:15][CH:14]=3)[CH:10]=2)[NH:5][C:4]1=[O:30].C1COCC1.[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([C:43]2[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][CH:44]=2)[CH2:39][CH2:38]1>CCOC(C)=O>[CH3:36][N:37]1[CH2:38][CH2:39][N:40]([C:43]2[CH:48]=[CH:47][C:46]([NH:49][CH:2]=[C:3]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][C:13]5[CH:14]=[CH:15][C:16]([NH:19][C:20]([C:22]6[N:23]([CH2:28][CH3:29])[N:24]=[C:25]([CH3:27])[CH:26]=6)=[O:21])=[CH:17][CH:18]=5)[CH:10]=4)[NH:5][C:4]3=[O:30])=[CH:45][CH:44]=2)[CH2:41][CH2:42]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 1784630622-ethyl-N-[4-[[3-(hydroxymethylidene)-2-oxo-1H-indol-5-yl]methyl]phenyl]-5-methylpyrazole-3-carboxamide

Product 1

HCID 178463061HCID 178463061, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide (prepared below, 70 mg, 0.175 mmol) and THF (1 mL). To the resulting solution was added 4-(4-Methyl-piperazin-1-yl)-phenylamine (66.8 mg, 0.349 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and then diluted with EtOAc (2 mL). The solution was washed with water (2 mL) and the water layer was re-washed with additional EtOAc (2 mL). The combined organic layers were then concentrated in vacuo affording the crude product. The crude product was further purified by silica gel column chromatography with 5% methanol in chloroform as eluant to give the desired product as a solid in 55% yield (55 mg, 0.96 mmol).

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. washThe solution was washed with water (2 mL)
  4. washthe water layer was re-washed with additional EtOAc (2 mL)
  5. concentrationThe combined organic layers were then concentrated in vacuo
  6. customaffording the crude product
  7. customThe crude product was further purified by silica gel column chromatography with 5% methanol in chloroform as eluant

Sources & evidence

ORD record
ord-099d4d3b51ce4054b735b54975d1806d
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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