Cyclohexylamine → 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid cyclohexylamide

HRID 229862Notes

Reaction equation

HRID 229862 reaction equation
[CH3:1][C:2]1[N:3]([CH2:21][C@@H:22]2[CH2:26][CH2:25][CH2:24][O:23]2)[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]([F:20])([F:19])[F:18])=[CH:5][C:6]=1[C:7](O)=[O:8].CN(C(O[N:35]1N=N[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.C1(N)CCCCC1>CN(C)C=O>[CH:36]1([NH:35][C:7]([C:6]2[CH:5]=[C:4]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][C:17]([F:18])([F:19])[F:20])[N:3]([CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)[C:2]=2[CH3:1])=[O:8])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 690199812-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 116193132-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid cyclohexylamideYield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 77 mg of 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid in 3 ml of dimethylformamide were added 74 mg of TBTU, 179 μl of N,N-diisopropylethylamine and 26 μl of cyclohexylamine and the reaction mixture was stirred at ambient temperature for 18 hours. After such time the reaction mixture was then concentrated in vacuo and purified by column chromatography (SiO2, heptane/ethyl acetate) to give 70 mg of the title compound as a colorless solid, MS (ISP) 451.5 (M+H)+.

Workup

  1. concentrationAfter such time the reaction mixture was then concentrated in vacuo
  2. custompurified by column chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-98c6549fcfc146cfbf597b08fa7994f7
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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