Tetrahydrofuran → HCID 117667080, compound

HRID 1526259Notes

Reaction equation

HRID 1526259 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C:12]1[CH:50]=[CH:49][CH:48]=[CH:47][C:13]=1[CH2:14][O:15][C:16]1[N:17]=[C:18]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:39][CH2:38][CH:37]([N:40]4[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]4)[CH2:36][CH2:35]3)=[CH:30][CH:29]=2)[C:19]([C:24]([NH2:26])=[O:25])=[N:20][C:21]=1[CH2:22][CH3:23].O1CCCC1.O.NN>C(O)C>[NH2:3][C:12]1[CH:50]=[CH:49][CH:48]=[CH:47][C:13]=1[CH2:14][O:15][C:16]1[N:17]=[C:18]([NH:27][C:28]2[CH:29]=[CH:30][C:31]([N:34]3[CH2:35][CH2:36][CH:37]([N:40]4[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]4)[CH2:38][CH2:39]3)=[CH:32][CH:33]=2)[C:19]([C:24]([NH2:26])=[O:25])=[N:20][C:21]=1[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 117667475HCID 117667475, compound

Product 1

HCID 117667080HCID 117667080, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)benzyl]oxy}-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (540 mg), tetrahydrofuran (10.8 mL), ethanol (10.8 mL), and hydrazine monohydrate (160 mg) was stirred at room temperature for 30 hours. The reactant was subjected to liquid separation by the addition of water and chloroform. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type: eluent; ethyl acetate, and then chloroform:methanol=97:3) to obtain 5-[(2-aminobenzyl)oxy]-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (315 mg) as a brown solid.

Workup

  1. customThe reactant was subjected to liquid separation by the addition of water and chloroform
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH2 type

Sources & evidence

ORD record
ord-4e858183dea142a7a458de1559416d09
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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