Sodium cyanoborohydride → [4-(5-Cyano-3-pyridin-3-yl-pyrazol-1-yl)phenyl]-(2-indanylmethyl)amine

HRID 1634112Notes

Reaction equation

HRID 1634112 reaction equation
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[N:6]=[C:5]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:4]=1)#[N:2].[CH2:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH:22]1[CH:30]=O.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:1]([C:3]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][CH2:30][CH:22]3[CH2:21][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:23]3)=[CH:12][CH:13]=2)[N:6]=[C:5]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 117447712,3-Dihydro-1H-indene-2-carbaldehydeHCID 186771061-(4-Aminophenyl)-3-(3-pyridyl)-5-cyanopyrazole

Product 1

HCID 18677104[4-(5-Cyano-3-pyridin-3-yl-pyrazol-1-yl)phenyl]-(2-indanylmethyl)amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 5-cyano-3-(3-pyridyl)-1-(4′-aminophenyl)pyrazole (185 mg, 0.7 mmol) and indane 2-carboxaldehyde (0.96 mmol, 140 mg) in methanol (9 mL) and acetic acid (1 mL) was stirred at room temp for 30 min. Sodium cyanoborohydride (124 mg, 2 mmol) was added and stirring continued at room temperature. After 3 h the solvent was evaporated under vacuum, and the residue was taken up in sodium bicarbonate solution (50 mL) and extracted with methylene chloride (3×50 mL). The combined extract was washed with water, dried over anhydrous sodium sulfate and evaporated. Chromatography of the residue over silica gel (eluant, 15% ethyl acetate in methylene chloride) gave the title compound as a cream colored solid, m.p. 156-158° C. 1H NMR (DMSO-d6): δ 2.68-2.82 (3H, m), 3.05-3.15 (4H, m), 6.36-6.42 (1H, br. t), 6.75-6.77 (2H, d, J=8.9 Hz), 7.09-7.15 (2H, m), 7.21-7.24 (4H, m), 7.45-7.47 (2H, d, J=8.8 Hz), 7.51-7.54 (1H, m), 7.98 (1H, s), 8.21-8.28 (1H, br. d.), 8.6-8.62 (1H, br. d.), 9.1 (1H, d, J=1.9 Hz).

Workup

  1. customcontinued at room temperature
  2. customAfter 3 h the solvent was evaporated under vacuum
  3. extractionextracted with methylene chloride (3×50 mL)
  4. extractionThe combined extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-36bc714d8b6042ee9ae5af4aabd36660
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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