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

HRID 1019689Notes

Reaction equation

HRID 1019689 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)[O:24]C4C=CC([N+]([O-])=O)=CC=4)[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:44]([C:47]1[CH:51]=[C:50]([CH2:52][OH:53])[O:49][N:48]=1)(=[O:46])[NH2:45]>ClCCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:53][CH2:52][C:50]4[O:49][N:48]=[C:47]([C:44](=[O:46])[NH2:45])[CH:51]=4)[CH2:18][CH2:19]3)=[N:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 80272465-(Hydroxymethyl)-1,2-oxazole-3-carboxamideHCID 666608374-nitrophenyl 2-[5'-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-ethylcarbamate

Product 1

HCID 462008953-Carbamoylisoxazol-5-ylmethyl 2-[5'-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]ethylcarbamate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 0.25 g (0.54 mmol) of 4-nitrophenyl 2-[5′-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-ethylcarbamate, prepared in step 1.5., 0.139 g (1.08 mmol) of N,N-diisopropylethylamine, 0.033 g (0.27 mmol) of N,N-dimethylaminopyridine and 0.084 g (0.59 mmol) of 3-carbamoylisoxazol-5-ylmethanol in 5 mL of 1,2-dichloroethane is heated in a sealed tube at 90° C. for 12 hours.

Sources & evidence

ORD record
ord-eba7814b51204a35b562943becdb04d7
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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