1-[5-(4-Methyl-pyrazol-1-yl)-2-nitro-phenyl]-piperidine → 4-(4-Methyl-pyrazol-1-yl)-2-piperidin-1-yl-phenylamine

HRID 646876Notes

Reaction equation

HRID 646876 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:8]=[CH:9][C:10]([N+:19]([O-])=O)=[C:11]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:12]=2)[CH:6]=1>C1COCC1>[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:8]=[CH:9][C:10]([NH2:19])=[C:11]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:12]=2)[CH:6]=1

Participants

3

Reactant 1

HCID 686843421-[5-(4-Methyl-pyrazol-1-yl)-2-nitro-phenyl]-piperidine

Product 1

HCID 686821264-(4-Methyl-pyrazol-1-yl)-2-piperidin-1-yl-phenylamineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[5-(4-Methyl-pyrazol-1-yl)-2-nitro-phenyl]-piperidine (110 mg, 0.38 mmol, as prepared in the previous step) was allowed to react with TiCl3 (2.3 mL, 3.8 mmol) in 3 mL of THF. The reaction was quenched with satd aq NaHCO3 (15 mL) and poured into 25 mL of EtOAc. The organic layer was separated, washed with water (2×25 mL), dried (Na2SO4), and concentrated in vacuo to afford 94 mg (95%) of 4-(4-methyl-pyrazol-1-yl)-2-piperidin-1-yl-phenylamine, which was allowed to react in a similar manner to Example 4, step (c), with 5-cyano-furan-2-carbonyl chloride (84 mg, 0.54 mmol) in the presence of DIEA (137 μL, 0.79 mmol) to afford 52.7 mg (47%) of the title compound as a light yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 9.65 (s, 1H), 8.50 (d, 1H, J=8.8 Hz), 7.92 (s, 1H), 7.71 (s, 1H), 7.37 (dd, 1H, J=2.5, 8.8 Hz), 7.29 (d, 1H, J=3.8 Hz), 7.23 (d, 1H, J=3.7 Hz), 6.46-6.45 (m, 1H), 2.94-2.89 (m, 4H), 2.14 (s, 3H), 1.85-1.80 (m, 4H), 1.66 (br s, 2H); Mass spectrum (ESI, m/z): Calcd. for C21H21N5O2, 376.1 (M+H), found 376.1.

Workup

  1. customThe reaction was quenched with satd aq NaHCO3 (15 mL)
  2. additionpoured into 25 mL of EtOAc
  3. customThe organic layer was separated
  4. washwashed with water (2×25 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f5377ac2b5042889002e022e2f23c08
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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