4-Fluorobenzonitrile → HCID 178509997, compound

HRID 215951Notes

Reaction equation

HRID 215951 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:9]2=[O:18])[CH2:4][CH2:3]1.F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O.CO>[OH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][N:15]([C:20]4[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=4)[CH2:14][CH2:13]3)[C:9]2=[O:18])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 145174-FluorobenzonitrileHCID 81531DiisopropylethylamineHCID 178517869HCID 178517869, compound

Product 1

HCID 178509997HCID 178509997, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-(trans-4-hydroxycyclohexyl)-2,8-diazaspiro[4.5]decan-1-one (20 mg, 0.00008 mol), 4-fluorobenzonitrile (12.3 mg, 0.000102 mol) and N,N-diisopropylethylamine (44 μL, 0.00025 mol) in N-methylpyrrolidinone (0.5 mL) was irradiated under microwave at 200° C. for 15 min. The mixture was diluted with methanol (1.3 mL), and purified by Prep-HPLC to give 4-[2-(trans-4-hydroxycyclohexyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]benzonitrile. LCMS: (M+H)+=354.2.

Workup

  1. customwas irradiated under microwave at 200° C. for 15 min
  2. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-5085597d6bc2481c91f9f96fc6a6dd71
Source dataset
uspto-grants-2012_06
Patent number
US08193207B2

Reaction notes

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