2-Fluorobenzoic acid → HCID 69052796, compound

HRID 729611Notes

Reaction equation

HRID 729611 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[N:6][CH:5]=1)([O-:3])=[O:2].[F:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](O)=[O:25].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[F:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([N:18]1[CH2:19][CH2:20][CH:15]([O:14][C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][N:6]=2)[CH2:16][CH2:17]1)=[O:25]

Participants

6

Reactant 4

HCID 99352-Fluorobenzoic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 69054059HCID 69054059, compound

Product 1

HCID 69052796HCID 69052796, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stir a reaction mixture of 4-(4-nitro-isoquinoline-1-yloxy)-piperidine (4.0 g, 14.6 mmol), 2-fluorobenzoic acid (2.45 g, 17.5 mmol), DCC (3.6 g, 17.5 mmol), and HOBt (2.37 g, 17.5 mmol) in THF (100 mL) at 22° C. overnight. Filter then concentrate. Subject residue to silica gel chromatography eluting with hexanes and ethyl acetate to provide (2-fluoro-phenyl)-[4-(4-nitro-isoquinoline-1-yloxy)-piperidin-1-yl]-methanone as a yellow solid (6.82 g, 92% yield, ES+ (m/z) 396.3 [M+H]).

Workup

  1. filtrationFilter
  2. concentrationthen concentrate
  3. washSubject residue to silica gel chromatography eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-894f0911b66d4b9e97293c3422571c64
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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