1-(2-Nitro-5-pyrazol-1-yl-phenyl)-piperidine → 2-Piperidin-1-yl-4-pyrazol-1-yl-phenylamine

HRID 32909

Reaction equation

HRID 32909 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][CH:12]=[N:11]2)=[CH:6][C:5]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([O-])=O>C1COCC1>[N:15]1([C:5]2[CH:6]=[C:7]([N:10]3[CH:14]=[CH:13][CH:12]=[N:11]3)[CH:8]=[CH:9][C:4]=2[NH2:1])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

3

Reactant 1

HCID 693093521-(2-Nitro-5-pyrazol-1-yl-phenyl)-piperidine

Product 1

HCID 693102242-Piperidin-1-yl-4-pyrazol-1-yl-phenylamineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using a procedure similar to Example 4, step (b), 1-(2-nitro-5-pyrazol-1-yl-phenyl)-piperidine (100 mg, 0.31 mmol, as prepared in the previous step) was allowed to react with TiCl3 (1.80 mL, 2.94 mmol) in 3 mL of THF to afford 72 mg (94%) of 2-piperidin-1-yl-4-pyrazol-1-yl-phenylamine, which was allowed to react in a manner similar to Example 3, step (d), with 5-cyano-furan-2-carbonyl chloride (67.5 mg, 0.43 mmol) in the presence of DIEA (111 μL, 0.6 mmol) to afford 52.7 mg (47%) of the title compound as a light yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 9.67 (s, 1H), 8.50 (d, 1H, J=8.8 Hz), 7.90 (d, 1H, J=2.4 Hz), 7.71 (d, 1H, J=1.5 Hz), 7.65 (d, 1H, J=2.4 Hz), 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), 2.92-2.89 (m, 4H), 1.85-1.80 (m, 4H), 1.66 (br s, 2H); Mass spectrum (ESI, m/z): Calcd. for C20H19N5O2 362.1 (M+H), found 362.2.

Workup

  1. customas prepared in the previous step)

Sources & evidence

ORD record
ord-d8e21add104547a0aab4646ae62b878e
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Linked notes

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