Hydrochloric Acid → HCID 86646071, compound

HRID 1800674Notes

Reaction equation

HRID 1800674 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([C:12]([NH:14][C:15]2[CH:16]=[C:17]([NH:21][C:22]3[N:27]=[C:26]([S:28][C:29]#[N:30])[C:25]([N+:31]([O-])=O)=[CH:24][N:23]=3)[CH:18]=[CH:19][CH:20]=2)=[O:13])[CH:9]=[CH:10][CH:11]=1)([CH3:5])[CH3:4])#[N:2].CN1CCCC1=O.Cl.[OH-].[Na+]>C(O)C>[NH2:30][C:29]1[S:28][C:26]2[N:27]=[C:22]([NH:21][C:17]3[CH:16]=[C:15]([NH:14][C:12](=[O:13])[C:8]4[CH:9]=[CH:10][CH:11]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=4)[CH:20]=[CH:19][CH:18]=3)[N:23]=[CH:24][C:25]=2[N:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 86646070HCID 86646070, compound

Product 1

HCID 86646071HCID 86646071, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 2-{[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenyl]amino}-5-nitropyrimidin-4-yl thiocyanate (844 mg, 1.84 mmol) and reduced iron (513 mg, 9.20 mmol) in ethanol (16 mL)/1-methylpyrrolidin-2-one (8 mL) was added 1N hydrochloric acid (4 mL), and the mixture was stirred at 100° C. for 1.5 hr. The reaction mixture was neutralized with 2N aqueous sodium hydroxide solution (3 mL), and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure. To the obtained residue was added saturated aqueous sodium hydrogen carbonate solution (50 mL), and the mixture was extracted with ethyl acetate (50 mL, 2×20 mL). The combined organic layer was washed with saturated brine (10 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=40/60→20/80), and the fractions containing the object product were concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate and hexane to give the title compound (477 mg, 60%) as pale-purple crystals.

Workup

  1. filtrationthe insoluble material was filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionTo the obtained residue was added saturated aqueous sodium hydrogen carbonate solution (50 mL)
  4. extractionthe mixture was extracted with ethyl acetate (50 mL, 2×20 mL)
  5. washThe combined organic layer was washed with saturated brine (10 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=40/60→20/80)
  10. additionthe fractions containing the object product
  11. concentrationwere concentrated under reduced pressure
  12. customThe obtained residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-e817f42ba19b43b6aa1048b6172b8834
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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