4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde → HCID 178526768, compound

HRID 2274388Notes

Reaction equation

HRID 2274388 reaction equation
[N+:1]([C:4]1[C:5]([CH:15]=O)=[N:6][N:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:8]=1)([O-:3])=[O:2].[F:17][C:18]1[CH:19]=[C:20]([NH2:34])[C:21]([NH2:33])=[CH:22][C:23]=1[O:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CO>[F:17][C:18]1[C:23]([O:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:22][C:21]2[NH:33][C:15]([C:5]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][N:7]([CH:9]4[CH2:14][CH2:13][CH2:12][CH2:11][O:10]4)[N:6]=3)=[N:34][C:20]=2[CH:19]=1

Participants

4

Reactant 2

HCID 224778374-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehydeHCID 688419974-Fluoro-5-(2-piperidin-1-ylethoxy)benzene-1,2-diamine

Product 1

HCID 178526768HCID 178526768, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 248 mg of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde and 278.9 mg of 4-fluoro-5-(2-piperidin-1-ylethoxy)benzene-1,2-diamine in 12 mL of methanol is stirred at ambient temperature overnight. In order for the reaction to be complete, heating is carried out for a further half an hour at reflux and then overnight at ambient temperature. After concentration under vacuum in a rotary evaporator, 515 mg of 5-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-(2-piperidin-1-ylethoxy)-1H-benzimidazoleare isolated in the form of a dark solid. 1H NMR (300 MHz, DMSO-d6, δ in ppm): for this batch, we observe a 60%-40% resolution of tautomers with: from 1.31 to 1.78 (m, 9H); from 1.87 to 2.30 (m, 3H); 2.46 (m partially masked, 4H); 2.72 (t, J=6.0 Hz, 2H); 3.69 (m, 1H); 4.00 (m, 1H); 4.19 (t, J=6.0 Hz, 2H); 5.60 (dd, J=2.0 and 9.0 Hz, 1H); 7.26 (d, J=7.5 Hz, 0.6H); 7.41 (d, J=11.5 Hz, 0.4H); 7.45 (d, J=7.5 Hz, 0.4H); 7.53 (d, J=11.5 Hz, 0.6H); 9.18 (s, 1H); 12.85 (broad m, 1H).

Workup

  1. customIn order for the reaction
  2. temperatureheating
  3. waitis carried out for a further half an hour
  4. temperatureat reflux
  5. customovernight
  6. customat ambient temperature
  7. concentrationAfter concentration under vacuum
  8. customin a rotary evaporator, 515 mg of 5-fluoro-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-(2-piperidin-1-ylethoxy)-1H-benzimidazoleare
  9. customisolated in the form of a dark solid

Sources & evidence

ORD record
ord-77ef7580ccf64e04bcd2a5f6534c53ad
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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