Triethylamine → HCID 66796035, compound

HRID 2043788Notes

Reaction equation

HRID 2043788 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[N:20]=[C:19]([C:21]([OH:23])=O)[CH:18]=[N:17]3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:34][NH:35][C@H:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH2:38][CH2:37]1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH3:34][N:35]([C@H:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH2:38][CH2:37]1)[C:21]([C:19]1[CH:18]=[N:17][N:16]([CH:13]2[CH2:12][CH2:11][N:10]([C:8](=[O:9])[CH2:7][N:6]3[C:2]([CH3:1])=[CH:3][C:4]([C:24]([F:26])([F:25])[F:27])=[N:5]3)[CH2:15][CH2:14]2)[N:20]=1)=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7128544(R)-N-Methyl-1,2,3,4-tetrahydronaphthalen-1-amineHCID 67463041HCID 67463041, compound2×

Product 1

HCID 66796035HCID 66796035, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-2H-1,2,3-triazole-4-carboxylic acid (0.070 g, 0.18 mmol) (i.e. the product of Example 32, Step C) in dichloromethane (2 mL) was added oxalyl chloride (0.05 mL, 0.35 mmol) and one drop of N,N-dimethylformamide. After 45 minutes the reaction mixture was concentrated in vacuo and the resulting residue was dissolved in dichloromethane (10 mL). The reaction mixture was then added to a solution of (R)—N-methyl-1,2,3,4-tetrahydronaphthalen-1-ylamine (32 mg, 0.20 mmol) and triethylamine (0.033 mL, 0.24 mmol) in dichloromethane (2 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. The organic layer was washed with saturated aqueous sodium bicarbonate, dried (Na2SO4) and the solvent was removed with a rotary evaporator. The residue was purified by medium pressure liquid chromatography (MPLC) using 35-60% ethyl acetate in hexanes as eluant to afford 74 mg of the title product, a compound of the present invention as an oil.

Workup

  1. concentrationAfter 45 minutes the reaction mixture was concentrated in vacuo
  2. dissolutionthe resulting residue was dissolved in dichloromethane (10 mL)
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed with a rotary evaporator
  6. customThe residue was purified by medium pressure liquid chromatography (MPLC)

Sources & evidence

ORD record
ord-933911e859034dd28edf332beab3a10a
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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