4-Fluorobenzoyl chloride → HCID 21362791, compound

HRID 1168869Notes

Reaction equation

[CH:1]([NH:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][N:14]([CH:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][C:21]([NH2:27])=[CH:22][CH:23]=3)[CH2:18]2)[CH2:15][CH3:16])[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[F:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>ClCCl.CCN(C(C)C)C(C)C>[CH:1]([NH:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([CH2:13][N:14]([CH2:15][CH3:16])[CH:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][C:21]([NH:27][C:33](=[O:34])[C:32]4[CH:36]=[CH:37][C:29]([F:28])=[CH:30][CH:31]=4)=[CH:22][CH:23]=3)[CH2:18]2)[CH2:11][CH2:12]1)=[O:6])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4-{[(7-amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-ethyl-amino]-methyl}-piperidine-1-carboxylic acid isopropylamide (200 μL of 0.25 M in acetonitrile, 50 μmol) was added 220 μL of a 0.25 M solution of 4-fluorobenzoyl chloride in dichloromethane and 30 μL of DIEA. The solution was allowed to stir for 24 h at 25° C. under N2 and concentrated in vacuo. The final product was isolated by preparative RPHPLC (YMC Combiprep ODS-A column, 10-90% acetonitrile:water (0.1% TFA)) to afford 4-({ethyl-[7-(4-fluoro-benzoylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid isopropylamide (13.1 mg) 7 [M+H]+=495.

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0d87825dcb584459a25d85b1160e0af2
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06627644B2

Reaction notes

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