Sodium cyanoborohydride → HCID 18677097, compound

HRID 1634117Notes

Reaction equation

HRID 1634117 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.[Cl: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[Cl: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 5003444Sodium cyanoborohydrideHCID 124670502-Chloro-6-methylbenzaldehydeHCID 186771061-(4-Aminophenyl)-3-(3-pyridyl)-5-cyanopyrazole

Product 1

HCID 18677097HCID 18677097, compoundYield 76%

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-chloro-6-methylbenzaldehyde (0.9 g) in acetic acid (4 mL) and MeOH (7 mL) at room temperature was added sodium cyanoborohydride (79 mg, 1.25 mmol). The reaction mixture was stirred at room temperature for 16 h 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 chromatographed on silica gel (eluant, gradient of 15-25% EtOAc in CH2Cl2) to provide the title compound (152 mg, 76%). NMR (CDCl3, 400 MHz): 9.2 (s, 1H); 8.7(br, 1H); 8.4(br, 1H); 7.6-7.5 (overlapping m, 3H), 7.4-7.1(overlapping m, 5H), 6.8 (d, 2H), 4.5 (s, 2H), 2.5 (s, 3H).

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. customwas chromatographed on silica gel (eluant, gradient of 15-25% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-f5be28ca6da34a73bcafbed88c812725
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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