Methylamine → {5-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazol-3-yl}methyl methylcarbamate

HRID 733141Notes

Reaction equation

HRID 733141 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][C:20]([F:23])([F:22])[F:21])[CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([CH2:24][OH:25])[CH:3]=1.[C:26](N1C=CN=C1)([N:28]1C=CN=[CH:29]1)=[O:27].CN>ClCCl>[CH3:29][NH:28][C:26](=[O:27])[O:25][CH2:24][C:4]1[CH:3]=[C:2]([CH3:1])[N:6]([C:7]2[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][C:20]([F:22])([F:23])[F:21])[CH:10]=[CH:11][CH:12]=2)[N:5]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 11187128{5-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazol-3-yl}methanol

Product 1

HCID 11223447{5-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazol-3-yl}methyl methylcarbamateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of the alcohol from EXAMPLE 123 (0.050 g, 0.14 mmol) in dry dichloromethane (3 mL) was added 1,1′-carbonyldiimidazole (0.023 g, 0.14 mmol). The reaction solution was stirred at room temperature for one hour before the methylamine was added. The reaction was then stirred at the same temperature for overnight. The reaction was quenched with 10% HCl aqueous, and extracted with dichloromethane (3 times). The combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The product was purified via a column chromatography on silica gel. The carbamate was obtained as a white solid, 0.0565 g, 97% yield.

Workup

  1. additionwas added
  2. customThe reaction was quenched with 10% HCl aqueous
  3. extractionextracted with dichloromethane (3 times)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe product was purified via a column chromatography on silica gel

Sources & evidence

ORD record
ord-1e0487c038cd4a20a8bf7e46bb4677a4
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

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