N-methyl-2-pyrrolidone → 7-[5-(Trifluoromethyl)pyridin-2-yl]-2,7-diazaspiro[4.5]decan-1-one

HRID 1044367Notes

Reaction equation

HRID 1044367 reaction equation
[C:1]1(=[O:11])[C:5]2([CH2:10][CH2:9][CH2:8][NH:7][CH2:6]2)[CH2:4][CH2:3][NH:2]1.Cl[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=1.C(N(CC)C(C)C)(C)C.CN1CCCC1=O>>[F:20][C:19]([F:22])([F:21])[C:16]1[CH:17]=[CH:18][C:13]([N:7]2[CH2:8][CH2:9][CH2:10][C:5]3([C:1](=[O:11])[NH:2][CH2:3][CH2:4]3)[CH2:6]2)=[N:14][CH:15]=1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 231351962,7-Diazaspiro[4.5]decan-1-one

Product 1

HCID 667223017-[5-(Trifluoromethyl)pyridin-2-yl]-2,7-diazaspiro[4.5]decan-1-one

Procedure

A mixture of 2,7-diazaspiro[4.5]decan-1-one (50.0 mg, 0.000324 mol), 2-chloro-5-(trifluoromethyl)pyridine (71 mg, 0.00039 mol) and N,N-diisopropylethylamine (0.17 mL, 0.00097 mol) in N-methylpyrrolidinone (2 mL, 0.02 mol) was irradiated with microwaves at 180° C. for 20 min. The product was purified by prep-HPLC. LC-MS: 300.2 (M+H)+.

Workup

  1. customwas irradiated with microwaves at 180° C. for 20 min
  2. customThe product was purified by prep-HPLC

Sources & evidence

ORD record
ord-cfe25265dd9140e9b5c61bf41a7a0d3f
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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