2,6-Dimethylbenzaldehyde → HCID 18677161, compound

HRID 1634115Notes

Reaction equation

HRID 1634115 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]#[N:14])=[CH:11][C:10]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH:24]=O.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[C:13]([C:12]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][CH2:24][C:23]3[C:26]([CH3:30])=[CH:27][CH:28]=[CH:29][C:22]=3[CH3:21])=[CH:7][CH:6]=2)[N:9]=[C:10]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:11]=1)#[N:14]

Participants

6

Reactant 3

HCID 5838412,6-DimethylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 186771061-(4-Aminophenyl)-3-(3-pyridyl)-5-cyanopyrazole

Product 1

HCID 18677161HCID 18677161, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(4-aminophenyl)-3-(3-pyridyl)-5-cyanopyrazole (130 mg, 0.5 mmol) and 2,6-dimethylbenzaldehyde (0.9 g) in acetic acid (2 mL) and MeOH (5 mL) at room temperature was added sodium cyanoborohydride (79 mg, 1.25 mmol). The reaction mixture was stirred at room temperature for 18 hr and then concentrated under a stream of nitrogen, diluted with water, extracted into ethyl acetate, washed with sodium bicarbonate solution, water and dried (MgSO4). The residue obtained on concentration was flash chromatographed on silica gel (elution with a gradient of 15-25% EtOAc in CH2Cl2) providing the title compound (142 mg, 75%). NMR (CDCl3, 400 MHz): 9.1 (s, 1H); 8.7 (br, 1H); 8.3 (d, 1H); 7.6 (d, 2H), 7.5 (m, 1H), 7.35 (s, 1H); 7.2 (m, 1H), 7.1 (overlapping m, 2H), 6.8 (d, 2H), 4.3 (s, 2H), 2.4 (s, 6H).

Workup

  1. concentrationconcentrated under a stream of nitrogen
  2. additiondiluted with water
  3. extractionextracted into ethyl acetate
  4. washwashed with sodium bicarbonate solution, water
  5. dry with materialdried (MgSO4)
  6. customThe residue obtained on concentration
  7. customchromatographed on silica gel (
  8. washelution with a gradient of 15-25% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-1020efba023149138fae8f8263d5aa2d
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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