Acetic Acid → HCID 9889126, compound

HRID 1634121Notes

Reaction equation

HRID 1634121 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:11]=[C:10]([C:12]#[N:13])[N:9]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[N:8]=2)[CH:2]=1.CC(O)=O.[C:25]([CH:27](C)[CH2:28][CH2:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1)#[N:26].[BH3-]C#N.[Na+]>CO>[C:12]([C:10]1[N:9]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][CH2:35][C:34]3[CH:33]=[CH:32][C:31]([O:30][CH2:29][CH2:28][CH2:27][C:25]#[N:26])=[CH:38][CH:37]=3)=[CH:18][CH:19]=2)[N:8]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:11]=1)#[N:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 186771061-(4-Aminophenyl)-3-(3-pyridyl)-5-cyanopyrazoleHCID 18677127HCID 18677127, compound

Product 1

HCID 9889126HCID 9889126, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-(3-Pyridyl)-5-cyano-1-(4′-aminophenyl)pyrazole (0.5 mmol) was dissolved in MeOH (4 mL) and treated with HOAc (4 mL). The reaction was treated with a solution of 4-(3-cyanobutoxy)benzaldehyde (from Example above) (0.75 mmol) in MeOH (1 mL) and stirred at room temperature for 30 minutes. NaCNBH3 (1.25 mmol) was added in one portion. After 2 hr, volatiles were removed, the residue taken up in water, neutralized with NaHCO3 (aq) and extracted with dichloromethane. Organic extracts were combined, dried over MgSO4 and concentrated to leave a clear oil. Pure product was eluted from silica gel column using 50% dichloromethane in EtOAc giving a light yellow solid (140 mg, 64%), m.p. 128-129° C. 1H NMR (CDCl3): δ 1.98-2.04 (m, 2H), 2.63-2.66 (t, J=7.1 Hz, 2H), 4.00-4.04 (t, J=6 Hz, 2H), 4.27-4.29 (d, J=5.8 Hz, 2H), 6.72-6.79 (m, 3H), 6.92-6.94 (d, J=8.5 Hz, 2H), 7.31-7.33 (d, J=8.5 Hz, 2H), 7.42-7.44 (d, J=8.7 Hz, 2H), 7.50-7.53 (m, 1H), 7.96 (s, 1H), 8.24-8.26 (d, J=8 Hz, 1H), 8.60-8.61 (d, J=4.6 Hz, 1H), 9.10 (s, 1H).

Workup

  1. waitAfter 2 hr
  2. customvolatiles were removed
  3. extractionextracted with dichloromethane
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto leave a clear oil
  7. washPure product was eluted from silica gel column

Sources & evidence

ORD record
ord-4883df581d1a451b92cd1a0ac8714dde
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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