Water → tert-butyl methyl(2-(methyl((3-(4-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate

HRID 570780Notes

Reaction equation

HRID 570780 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14](C=O)=[CH:13][N:12]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:23][N:24]([CH2:32][CH2:33][NH:34][CH3:35])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].[BH3-][C:37]#N.[Na+].O>CO.[Cl-].[Cl-].[Zn+2]>[CH3:23][N:24]([CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][C:14]1[C:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[N:11][N:12]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[CH:13]=1)[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 14403871tert-Butyl methyl(2-(methylamino)ethyl)carbamateHCID 904258773-(4-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 90425474tert-butyl methyl(2-(methyl((3-(4-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamateYield 89.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 3-(4-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde (0.550 g, 0.00182 mol) in methanol (10 mL) at room temperature were added TEA (221 mg, 0.00913 mol), ZnCl2 (0.025 g, 0.000182 mol) and tert-butyl methyl(2-(methylamino)ethyl)carbamate (0.410 g, 0.00219 mol) and stirred for 45 min. NaCNBH3 (0.580 g, 0.00913 mol) was added and the reaction mixture was stirred for 2 h at room temperature. The reaction was poured into water (70 mL) and extracted with EtOAc (70 mL×2). The combined extracts were washed with brine (100 mL), dried over sodium sulphate and concentrated under vacuum. The residue was purified by SGC using DCM:MeOH (0%-4%) as eluent to obtain tert-butyl methyl(2-(methyl((3-(4-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate (0.770 g, Yield: 86.71%). LCMS (ESI): RT=2.00 min, m/z=474.8 [M+F1]+.

Workup

  1. stirringthe reaction mixture was stirred for 2 h at room temperature
  2. extractionextracted with EtOAc (70 mL×2)
  3. washThe combined extracts were washed with brine (100 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by SGC

Sources & evidence

ORD record
ord-d927fbb8382b456ca85eae39ca869764
Source dataset
uspto-grants-2015_05
Patent number
US09023883B2

Reaction notes

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