Diisopropylethylamine → HCID 57377350, compound

HRID 1184387Notes

Reaction equation

HRID 1184387 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=[C:10]([C:20](O)=[O:21])[CH:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:24][O:25]/[N:26]=[C:27]1/[C@@H:28]([NH2:33])[CH2:29][CH2:30][CH2:31][CH2:32]/1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:24][O:25]/[N:26]=[C:27]1/[C@@H:28]([NH:33][C:20]([C:10]2[CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:13]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)=[O:21])[CH2:29][CH2:30][CH2:31][CH2:32]/1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66687043HCID 66687043, compoundHCID 88536646HCID 88536646, compound

Product 1

HCID 57377350HCID 57377350, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.050 g 4-(4-chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid in 2.0 ml dimethylformamide was added 0.030 g (S)-2-amino-cyclohexanone-(E)-O-methyl-oxime hydrochloride, 0.053 g TBTU and 0.097 g N,N-diisopropyl ethyl amine and the mixture was stirred at room temperature for 16 h. The solvent was evaporated under high vacuum and the residue was purified by chromatography on silica gel with a gradient of heptane to ethyl acetate to yield 0.045 g of the title compound as colorless oil. MS (EI): 465.1 (M+H).

Workup

  1. customThe solvent was evaporated under high vacuum
  2. customthe residue was purified by chromatography on silica gel with a gradient of heptane to ethyl acetate

Sources & evidence

ORD record
ord-229f1f60bb3a4c60bdcc97f17a73b6e4
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

Loading…