N-methyl-2-pyrrolidone → HCID 178517867, compound

HRID 215954Notes

Reaction equation

HRID 215954 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:19]C1C=CC(C#N)=CC=1.C(N(CC)C(C)C)(C)C.[CH3:37][N:38]1[CH2:42][CH2:41][CH2:40][C:39]1=O>CO>[F:19][C:40]1[C:39]([N:15]2[CH2:16][CH2:17][C:10]3([C:9](=[O:18])[N:8]([C@H:5]4[CH2:4][CH2:3][C@@H:2]([OH:1])[CH2:7][CH2:6]4)[CH2:12][CH2:11]3)[CH2:13][CH2:14]2)=[N:38][CH:37]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 145174-FluorobenzonitrileHCID 81531DiisopropylethylamineHCID 178517868HCID 178517868, compound

Product 1

HCID 178517867HCID 178517867, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(cis-4-hydroxycyclohexyl)-2,8-diazaspiro[4.5]decan-1-one (20 mg, 0.08 mmol), 4-fluorobenzonitrile (12.3 mg, 0.102 mmol) and N,N-diisopropylethylamine (44 μL, 0.25 mmol) 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 8-(3-fluoropyridin-2-yl)-2-(cis-4-hydroxycyclohexyl)-2,8-diazaspiro[4.5]decan-1-one. LCMS: (M+H)+=348.2.

Workup

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

Sources & evidence

ORD record
ord-ddb3c87384b5485fae1eeea2179bf07b
Source dataset
uspto-grants-2012_06
Patent number
US08193207B2

Reaction notes

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