(S)-morpholine-3-carboxylic acid → (3S)-4-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(4-(2-methoxy-2-oxoethyl)thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acid

HRID 524647Notes

Reaction equation

HRID 524647 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]=[C:25]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[N:26]=2)=[N:10]1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][C@H:33]1[C:38]([OH:40])=[O:39]>>[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]=[C:25]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[N:26]=2)[NH:12][C:13]([CH2:20][N:32]2[CH2:37][CH2:36][O:35][CH2:34][C@H:33]2[C:38]([OH:40])=[O:39])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 1501894(S)-morpholine-3-carboxylic acidHCID 118107623Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(4-(2-methoxy-2-oxoethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107609(3S)-4-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(4-(2-methoxy-2-oxoethyl)thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acidYield 60%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(4-(2-methoxy-2-oxoethyl)thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (1.15 g, 2 mmol) was reacted with (S)-morpholine-3-carboxylic acid (0.39 g, 3 mmol) according to the procedure as described in Example 1, Step C to give the title compound as a yellow solid (0.75 g, 60%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-1df32b4a7bbd4418b15dbb6d3c2715f9
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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