Tetrahydrofuran → HCID 178480711, compound

HRID 641053Notes

Reaction equation

HRID 641053 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=1)[C:12]([C:14]1[CH:22]=[C:21]2[C:17](/[C:18](=[CH:24]/O)/[C:19](=[O:23])[NH:20]2)=[CH:16][CH:15]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=2)[CH2:37][CH2:36]1>CCOC(C)=O>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=1)[C:12]([C:14]1[CH:22]=[C:21]2[C:17](/[C:18](=[CH:24]/[NH:47][C:44]3[CH:45]=[CH:46][C:41]([N:38]4[CH2:37][CH2:36][N:35]([CH3:34])[CH2:40][CH2:39]4)=[CH:42][CH:43]=3)/[C:19](=[O:23])[NH:20]2)=[CH:16][CH:15]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 178517286HCID 178517286, compound

Product 1

HCID 178480711HCID 178480711, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 6-(3-Benzylamino-benzoyl)-3-[1-hydroxy-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one (prepared below, 0.021 g, 0.056 mmol) and THF (1 mL). To the resulting solution was added 4-(4-Methyl-piperazin-1-yl)-phenylamine (10.7 mg, 0.056 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature. The yellow solid was dissolved in 5 mL of a solvent mixture containing 98% EtOAc/2% i-prOH and washed with water (2×5 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was chromatographed over silica (95/5 chloroform/Hexanes w/0.5% NEt3) to afford the title compound in 51% yield (15.5 mg, 0.028 mmol).

Workup

  1. customA small screw cap test tube
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with water (2×5 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was chromatographed over silica (95/5 chloroform/Hexanes w/0.5% NEt3)

Sources & evidence

ORD record
ord-c39eda2254bd471486a0c716339d2e9f
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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