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

HRID 1019688Notes

Reaction equation

HRID 1019688 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.[CH3:44][NH:45][C:46]([C:48]1[CH:52]=[C:51]([CH2:53][OH:54])[O:50][N:49]=1)=[O:47]>>[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:54][CH2:53][C:51]4[O:50][N:49]=[C:48]([C:46](=[O:47])[NH:45][CH3:44])[CH:52]=4)[CH2:18][CH2:19]3)=[N:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 110948685-(Hydroxymethyl)-N-methylisoxazole-3-carboxamideHCID 666608374-nitrophenyl 2-[5'-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-ethylcarbamate

Product 1

HCID 462008943-Methylcarbamoylisoxazol-5-ylmethyl 2-[5'-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]ethylcarbamateYield 82.1%

Procedure

The process is performed according to the procedure described in Example 1 (step 1.6.). Starting with 0.20 g (0.43 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.), 0.122 g (0.95 mmol) of N,N-diisopropylethylamine, 0.026 g (0.22 mmol) of N,N-dimethylaminopyridine and 0.074 g (0.47 mmol) of 3-methylcarbamoylisoxazol-5-ylmethanol, and after chromatography on silica gel, eluting with a 98/2/0.2 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.170 g of pure product is obtained in the form of a white powder.

Workup

  1. washafter chromatography on silica gel, eluting with a 98/2/0.2 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record
ord-b4be56db629f4a1caa632370f175df23
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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