1,2-Dichloroethane → 1-(cyclohexylacetyl)-4-((1R,2S)-2-{2-[4-(1H-tetrazol-1-yl)phenoxy]ethyl}cyclopropyl)piperidine

HRID 1850770Notes

Reaction equation

HRID 1850770 reaction equation
[N:1]1([C:6]2[CH:23]=[CH:22][C:9]([O:10][CH2:11][CH2:12][C@@H:13]3[CH2:15][C@@H:14]3[CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[CH:24]1([CH2:30][C:31](O)=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH:24]1([CH2:30][C:31]([N:19]2[CH2:20][CH2:21][CH:16]([C@H:14]3[CH2:15][C@H:13]3[CH2:12][CH2:11][O:10][C:9]3[CH:8]=[CH:7][C:6]([N:1]4[CH:5]=[N:4][N:3]=[N:2]4)=[CH:23][CH:22]=3)[CH2:17][CH2:18]2)=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 21363Cyclohexaneacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 867111854-((1R,2S)-2-(2-(4-(1H-tetrazol-1-yl)phenoxy)ethyl)cyclopropyl)piperidine

Product 1

HCID 708560481-(cyclohexylacetyl)-4-((1R,2S)-2-{2-[4-(1H-tetrazol-1-yl)phenoxy]ethyl}cyclopropyl)piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 23 mg (0.071 mmol) of 4-((1R,2S)-2-{2-[4-(1H-tetrazol-1-yl)phenoxy]ethyl}cyclopropyl)piperidine in 0.6 ml anhydrous N,N-dimethylformamide at ambient temperature was added 0.020 ml (0.14 mmol) cyclohexylacetic acid, followed by 27 mg (0.14 mmol) EDC, 9.6 mg (0.071 mmol) HOBt, and 0.062 ml (0.35 mmol) diisopropylethylamine. The solution was stirred overnight at ambient temperature. The crude in N,N-dimethylformamide was purified directly by reverse phase HPLC (TMC Pro-Pac C18; 30-100% acetonitrile/0.1% formic acid in water gradient). The pure fractions were lyophilized to yield the title compound as white solid.

Workup

  1. customThe crude in N,N-dimethylformamide was purified directly by reverse phase HPLC (TMC Pro-Pac C18; 30-100% acetonitrile/0.1% formic acid in water gradient)

Sources & evidence

ORD record
ord-b3b30a0e27df4280a14fbc71fa44e6e3
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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