N-methyl-2-pyrrolidone → 2-(4-Methylpyridin-3-yl)-7-[5-(trifluoromethyl)pyridin-2-yl]-2,7-diazaspiro[4.5]decan-1-one

HRID 1639987Notes

Reaction equation

HRID 1639987 reaction equation
Cl.Cl.Cl.[CH3:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[NH:11][CH2:12][CH2:13][C:14]1([C:20]([O:22]CC)=O)[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1.Cl[C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=1.C(N(CC)C(C)C)(C)C.CN1CCCC1=O.[H-].[Na+]>>[CH3:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][C:14]2([CH2:19][CH2:18][CH2:17][N:16]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=3)[CH2:15]2)[C:20]1=[O:22]

Participants

6

Reactant 5

HCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 81531DiisopropylethylamineHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 66722530Ethyl 3-(2-[(4-methylpyridin-3-yl)amino]ethyl}piperidine-3-carboxylate trihydrochloride

Product 1

HCID 579710432-(4-Methylpyridin-3-yl)-7-[5-(trifluoromethyl)pyridin-2-yl]-2,7-diazaspiro[4.5]decan-1-one

Procedure

A mixture of ethyl 3-{2-[(4-methylpyridin-3-yl)amino]ethyl}piperidine-3-carboxylate trihydrochloride (42.8 mg, 0.000107 mol), 2-chloro-5-(trifluoromethyl)pyridine (23 mg, 0.00013 mol) and N,N-diisopropylethylamine (0.056 mL, 0.00032 mol) in N-methylpyrrolidinone (0.8 mL, 0.008 mol) was irradiated with microwaves to 180° C. for 20 min. Sodium hydride (30.0 mg) was then added to the above solution and the mixture was stirred overnight. The product was purified by prep-HPLC. LC-MS: 391.2 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-233c3d3c59684002990f58970c0cc3f8
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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