Nitrogen → 1-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-1H-pyrazol-4-ylamine

HRID 2064921

Reaction equation

N#N.[CH3:3][C:4]1([C:9]2[O:13][C:12]([CH2:14][N:15]3[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[N:16]3)=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[O:13][C:12]([CH2:14][N:15]3[CH:19]=[C:18]([NH2:20])[CH:17]=[N:16]3)=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1

Participants

Conditions

Temperature: 75 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 1-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-4-nitro-1H-pyrazole (427 mg, 1.53 mmol), iron powder (258 mg, 4.59 mmol) and NH4Cl (413 mg, 7.65 mmol) in a mixture of EtOH (8.0 mL) and water (4.0 mL) was stirred at 75° C. for 2.5 h. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (30 mL) was added followed by 1M NaOH (30 mL). The aq. layer was extracted with CH2Cl2 (2×20 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a deep red oil. LC-MS-conditions 02: tR=0.58 min; [M+H]+=250.4.

Workup

filtrationThe reaction mixture was filtered while hot and
concentrationconcentrated under reduced pressure
additionCH2Cl2 (30 mL) was added
extractionThe aq. layer was extracted with CH2Cl2 (2×20 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-0951923b3d504c3ca7cdd9ccf2e90952
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Linked notes

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