Diisopropylethylamine → 3-Ethyl[1,2,4]oxadiazol-5-ylmethyl 2-[5'-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]ethylcarbamate

HRID 1019687Notes

Reaction equation

HRID 1019687 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][NH:22][C:23](=[O:34])[O:24][C:25]4C=CC([N+]([O-])=O)=C[CH:26]=4)[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH2:44]([C:46]1[N:50]=C(CO)[O:48][N:47]=1)[CH3:45]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][NH:22][C:23](=[O:34])[O:24][CH2:25][C:26]4[O:48][N:47]=[C:46]([CH2:44][CH3:45])[N:50]=4)[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 28063865(3-Ethyl-1,2,4-oxadiazol-5-yl)methanolHCID 666608374-nitrophenyl 2-[5'-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-ethylcarbamate

Product 1

HCID 462008933-Ethyl[1,2,4]oxadiazol-5-ylmethyl 2-[5'-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]ethylcarbamateYield 60.9%

Procedure

The process is performed according to the procedure described in Example 1 (step 1.6.). Starting with 0.23 g (0.5 mmol) of 4-nitrophenyl 2-[5′-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]ethylcarbamate, described in Example 1 (step 1.5.), 0.128 g (0.99 mmol) of N,N-diisopropylethylamine, 0.030 g (0.25 mmol) of N,N-dimethylaminopyridine and 0.067 g (0.50 mmol) of 3-ethyl[1,2,4]oxadiazol-5-ylmethanol, and after chromatography on silica gel, eluting with a 99/1/0.1 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.138 g of pure product is obtained in the form of a white powder.

Workup

  1. washafter chromatography on silica gel, eluting with a 99/1/0.1 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record
ord-3aa3e39356e74694b9fee5bb302c019f
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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