2-(Morpholin-3-yl)acetic acid hydrochloride → 2-(4-((6-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-phenyl-3,6-dihydropyrimidin-4-yl)methyl)morpholin-3-yl)acetic acid

HRID 524735Notes

Reaction equation

HRID 524735 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[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:10]1.Cl.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH:30]1[CH2:35][C:36]([OH:38])=[O:37]>>[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[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH:12][C:13]([CH2:20][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH:30]2[CH2:35][C:36]([OH:38])=[O:37])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 130995762-(Morpholin-3-yl)acetic acid hydrochlorideHCID 118107561Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-phenyl-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 732970492-(4-((6-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-phenyl-3,6-dihydropyrimidin-4-yl)methyl)morpholin-3-yl)acetic acidYield 49%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-phenyl-1,4-dihydropyrimidine-5-carboxylate (0.76 g, 1.53 mmol) (The compound was synthesized according to the procedure as described in WO2010069147) was reacted with 2-(morpholin-3-yl)acetic acid hydrochloride (0.28 g, 1.53 mmol) according to the procedure as described in Example 28 to give the title compound as a yellow solid (0.42 g, 49%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-cbf5aa6e7a50482385ed7c03db303522
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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