Water → HCID 117666121, compound

HRID 526772Notes

Reaction equation

HRID 526772 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([CH:16]=O)=[CH:14][N:13]([CH3:18])[N:12]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[CH2:19]([N:26]([CH3:31])[CH2:27][CH2:28][NH:29][CH3:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH3-]C#N.[Na+].O>CO.[Cl-].[Cl-].[Zn+2]>[CH2:19]([N:26]([CH3:31])[CH2:27][CH2:28][N:29]([CH2:16][C:15]1[C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[N:12][N:13]([CH3:18])[CH:14]=1)[CH3:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 66016N-Benzyl-N,N'-dimethylethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 43324280HCID 43324280, compound

Product 1

HCID 117666121HCID 117666121, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 3-(4-isopropoxyphenyl)-1-methyl-1H-pyrazole-4-carbaldehyde (82 mg, 0.32 mmol) in methanol (2 mL) was added TEA (129 mg, 1.2 mmol). ZnCl2 (5 mg, 0.05 mmol) and N-benzyl-N,N′-dimethylethane-1,2-diamine (71 mg, 0.38 mmol) were added at rt and stirred for 45 min. NaCNBH3 (87 mg, 1.2 mmol) was added and stirred for 2 h at rt. The reaction was poured into water (100 mL), extracted with EtOAc (50 mL×2). The combined extracts was washed with brine (100 mL), dried and concentrated under vacuum. The residue was purified by SGC using DCM: MeOH (0%-4%) as eluent to obtain N1-benzyl-N2-((3-(4-isopropoxyphenyl)-1-methyl-1H-pyrazol-4-yl)methyl)-N1,N2-dimethylethane-1,2-diamine (62 mg, Yield: 45%).

Workup

  1. stirringstirred for 2 h at rt
  2. extractionextracted with EtOAc (50 mL×2)
  3. washThe combined extracts was washed with brine (100 mL)
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by SGC

Sources & evidence

ORD record
ord-5ef8280224db48e1b974d694d0545469
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

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