Tetrahydrofuran → HCID 59652119, compound

HRID 606503Notes

Reaction equation

HRID 606503 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][N:14]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([N+:23]([O-])=O)[CH:16]=[N:15]2)=[CH:7][CH:6]=1)=[O:4].COC(C1C=CC(OCCN2C=C([N+]([O-])=O)C(C(OC)=O)=N2)=CC=1)=O.C1COCC1>[C].[Pd].CO>[NH2:23][C:17]1[CH:16]=[N:15][N:14]([CH2:13][CH2:12][O:11][C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)[C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 66768802HCID 66768802, compoundHCID 66769052HCID 66769052, compound

Product 1

HCID 59652119HCID 59652119, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of a mixture of methyl 1-[2-({4-[(methyloxy)carbonyl]phenyl}oxy)ethyl]-4-nitro-1H-pyrazole-5-carboxylate and methyl 1-[2-({4-[(methyloxy)carbonyl]phenyl}oxy)ethyl]-4-nitro-1H-pyrazole-3-carboxylate (7.42 g) in a mixed solvent of THF (200 mL)-methanol (100 mL) was added 10% palladium carbon (1.17 g), and the mixture was subjected to catalytic reduction under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered off, and the filtrate was concentrated. The precipitated methyl 4-amino-1-[2-({4-[(methyloxy)carbonyl]phenyl}oxy)ethyl]-1H-pyrazole-3-carboxylate (3.62 g) was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography to give methyl 4-amino-1-[2-({4-[(methyloxy)carbonyl]phenyl}oxy)ethyl]-1H-pyrazole-5-carboxylate (2.18 g).

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated
  5. filtrationThe precipitated methyl 4-amino-1-[2-({4-[(methyloxy)carbonyl]phenyl}oxy)ethyl]-1H-pyrazole-3-carboxylate (3.62 g) was filtered off
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d4c311a750746d98f752b710a58ecdb
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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