Morpholine-2-carboxylic acid hydrochloride → 4-((6-(2-bromo-4-fluorophenyl)-2-(3-cyano-1H-1,2,4-triazol-1-yl)-5-(ethoxycarbonyl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxylic acid

HRID 524702Notes

Reaction equation

HRID 524702 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]([N:22]2[CH:26]=[N:25][C:24]([C:27]#[N:28])=[N:23]2)=[N:10]1.Cl.[NH:30]1[CH2:35][CH2:34][O:33][CH:32]([C:36]([OH:38])=[O:37])[CH2:31]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]([N:22]2[CH:26]=[N:25][C:24]([C:27]#[N:28])=[N:23]2)[NH:12][C:13]([CH2:20][N:30]2[CH2:35][CH2:34][O:33][CH:32]([C:36]([OH:38])=[O:37])[CH2:31]2)=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 42614320Morpholine-2-carboxylic acid hydrochlorideHCID 90043056Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(3-cyano-1H-1,2,4-triazol-1-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 732967184-((6-(2-bromo-4-fluorophenyl)-2-(3-cyano-1H-1,2,4-triazol-1-yl)-5-(ethoxycarbonyl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxylic acidYield 42.3%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(3-cyano-1H-1,2,4-triazol-1-yl)-1,4-dihydropyrimidine-5-carboxylate (0.32 g, 0.63 mmol) was reacted with morpholine-2-carboxylic acid hydrochloride (0.13 g, 0.75 mmol) according to the procedure as described in Example 3 to give the title compound as a pale yellow solid (0.15 g, 42%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-eb180eee9172432381a6281b8d5a2887
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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