Trifluoroacetic acid → 8-(3-Chloropyridin-2-yl)-2-cyclohexyl-2,8-diazaspiro[4.5]decan-1-one

HRID 215945Notes

Reaction equation

HRID 215945 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][C:9]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:8]2=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][N:20]=1.C(N(CC)C(C)C)(C)C.FC(F)(F)C(O)=O>CN1CCCC1=O.CO>[Cl:25][C:24]1[C:19]([N:14]2[CH2:13][CH2:12][C:9]3([C:8](=[O:17])[N:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[CH2:11][CH2:10]3)[CH2:16][CH2:15]2)=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 588931652-Cyclohexyl-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 161189728-(3-Chloropyridin-2-yl)-2-cyclohexyl-2,8-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-cyclohexyl-2,8-diazaspiro[4.5]decan-1-one (20 mg, 0.00008 mol), 2,3-dichloropyridine (15.0 mg, 0.000102 mol) and N,N-diisopropylethylamine (44 μL, 0.00025 mol) in N-methylpyrrolidin-2-one (1.0 mL) was irradiated under microwave at 200° C. for 15 min. The mixture was adjusted acidic (pH to −2.0) with trifluoroacetic acid (TFA), and was diluted with methanol (0.8 mL). The resulting solution was purified by Prep-HPLC to give 8-(3-chloropyridin-2-yl)-2-cyclohexyl-2,8-diazaspiro[4.5]decan-1-one. LCMS: (M+H)+=348.20/350.20.

Workup

  1. customwas irradiated under microwave at 200° C. for 15 min
  2. customThe resulting solution was purified by Prep-HPLC

Sources & evidence

ORD record
ord-80edbc2bed8f46298483abeaaa409c1e
Source dataset
uspto-grants-2012_06
Patent number
US08193207B2

Reaction notes

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