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

HRID 1019691Notes

Reaction equation

HRID 1019691 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]4[CH:30]=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[N:48]=C(CO)[O:50][CH:51]=1)(=[O:46])[NH2:45]>>[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:30]4[O:50][CH:51]=[C:47]([C:44](=[O:46])[NH2:45])[N:48]=4)[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 66660756HCID 66660756, compoundHCID 666608374-nitrophenyl 2-[5'-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-ethylcarbamate

Product 1

HCID 461985364-Carbamoyloxazol-2-ylmethyl 2-[5'-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]ethylcarbamateYield 64.2%

Procedure

The process is performed according to the procedure described in Example 4. Starting with 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, described in Example 1 (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 4-carbamoyloxazol-2-ylmethanol, prepared in step 5.2., 0.162 g of pure product is obtained in the form of a white powder.

Workup

  1. customprepared in step 5.2

Sources & evidence

ORD record
ord-feba9007fec34019a5e087d3562b9963
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

Loading…