Ethanol → HCID 89709221, compound

HRID 1526181Notes

Reaction equation

HRID 1526181 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:14][C:15]2[C:16]([C:31]([NH2:33])=[O:32])=[N:17][CH:18]=[C:19]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=3)[N:20]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH2:34](O)C.N1(CO)C2C=CC=CC=2N=N1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:14][C:15]2[C:16]([C:31]([NH2:33])=[O:32])=[N:17][CH:18]=[C:19]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=3)[N:20]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:34])[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 702EthanolHCID 2241691H-Benzotriazole-1-methanolHCID 5049666Sodium triacetoxyborohydrideHCID 117667244HCID 117667244, compound

Product 1

HCID 89709221HCID 89709221, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-{[3-bromo-4-(piperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (523 mg) and ethanol (5 mL)-tetrahydrofuran (15 mL) were added 1H-benzotriazole-1-methanol (159 mg) and sodium triacetoxyborohydride (323 mg), followed by stirring at room temperature for 6 hours, then diluting with chloroform, and washing with a saturated aqueous sodium hydrogen carbonate solution. After the organic phase was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-50:1:0.1) to obtain 3-{[3-bromo-4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (447 mg) as a pale yellow solid.

Workup

  1. washwashing with a saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialAfter the organic phase was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-50:1:0.1)

Sources & evidence

ORD record
ord-e897d527009743e79fa5b991c6549fb4
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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