Hydrochloric Acid → HCID 117667029, compound

HRID 1526228Notes

Reaction equation

HRID 1526228 reaction equation
C1(C(=[N:14][C:15]2[CH:16]=[C:17]([O:21][C:22]3[N:23]=[C:24]([NH:33][C:34]4[CH:39]=[CH:38][C:37]([N:40]5[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]5)=[CH:36][CH:35]=4)[C:25]([C:30]([NH2:32])=[O:31])=[N:26][C:27]=3[CH2:28][CH3:29])[CH:18]=[N:19][CH:20]=2)C2C=CC=CC=2)C=CC=CC=1.Cl>O1CCCC1>[NH2:14][C:15]1[CH:16]=[C:17]([O:21][C:22]2[N:23]=[C:24]([NH:33][C:34]3[CH:35]=[CH:36][C:37]([N:40]4[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]4)=[CH:38][CH:39]=3)[C:25]([C:30]([NH2:32])=[O:31])=[N:26][C:27]=2[CH2:28][CH3:29])[CH:18]=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117666962HCID 117666962, compound

Product 1

HCID 117667029HCID 117667029, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-({5-[(diphenylmethylene)amino]pyridin-3-yl}oxy)-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (130 mg) and tetrahydrofuran (2.17 mL) was added 1 M hydrochloric acid (0.26 mL), followed by stirring at room temperature for 3 hours. To the residue obtained by evaporating the solvent was added ethyl acetate, followed by extraction with water. The aqueous phase was neutralized with a 1 M aqueous sodium hydroxide solution and extracted by the addition of a mixed solvent of chloroform:methanol (10:1). 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; chloroform:methanol=1:0-9:1) to obtain 5-[(5-aminopyridin-3-yl)oxy]-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (52 mg) as a yellow solid.

Workup

  1. customTo the residue obtained
  2. customby evaporating the solvent
  3. additionwas added ethyl acetate
  4. extractionfollowed by extraction with water
  5. extractionextracted by the addition of a mixed solvent of chloroform:methanol (10:1)
  6. washThe organic phase was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (NH2 type: eluent; chloroform:methanol=1:0-9:1)

Sources & evidence

ORD record
ord-efadfc0ab5d3483180cd7d596f76faa6
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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