4-Hydroxyproline → HCID 118107625, compound

HRID 524641Notes

Reaction equation

HRID 524641 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH2:20]Br)[NH:12][C:11]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[N:10]1.[OH:27][CH:28]1[CH2:32][NH:31][CH:30]([C:33]([OH:35])=[O:34])[CH2:29]1>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[N:10]=[C:11]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[NH:12][C:13]([CH2:20][N:31]2[CH2:32][CH:28]([OH:27])[CH2:29][CH:30]2[C:33]([OH:35])=[O:34])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 8254-HydroxyprolineHCID 59495567Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107625HCID 118107625, compoundYield 65%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (1.92 g, 3.81 mmol) was reacted with 4-hydroxypyrrolidine-2-carboxylic acid (0.5 g, 3.81 mmol) according to the procedure as described in Example 28 to give the title compound as a yellow solid (1.37 g, 65%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-5e9de7f6aab14db2b6c3ff7c9e485762
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

Loading…