2-(Morpholin-2-yl)acetic acid hydrochloride → 2-(4-((6-(2-bromo-4-fluorophenyl)-2-(1-(2-ethoxy-2-oxoethyl)-1H-1,2,4-triazol-3-yl)-5-(ethoxycarbonyl)-3,6-dihydropyrimidin-4-yl)methyl)morpholin-2-yl)acetic acid

HRID 524711Notes

Reaction equation

HRID 524711 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[N:26]=[CH:25][N:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:23]=2)=[N:10]1.Cl.[NH:34]1[CH2:39][CH2:38][O:37][CH:36]([CH2:40][C:41]([OH:43])=[O:42])[CH2:35]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[N:26]=[CH:25][N:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:23]=2)[NH:12][C:13]([CH2:20][N:34]2[CH2:39][CH2:38][O:37][CH:36]([CH2:40][C:41]([OH:43])=[O:42])[CH2:35]2)=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 452599202-(Morpholin-2-yl)acetic acid hydrochlorideHCID 118107556Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(1-(2-ethoxy-2-oxoethyl)-1H-1,2,4-triazol-3-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 1181075192-(4-((6-(2-bromo-4-fluorophenyl)-2-(1-(2-ethoxy-2-oxoethyl)-1H-1,2,4-triazol-3-yl)-5-(ethoxycarbonyl)-3,6-dihydropyrimidin-4-yl)methyl)morpholin-2-yl)acetic acidYield 53.3%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(1-(2-ethoxy-2-oxoethyl)-1H-1,2,4-triazol-3-yl)-1,4-dihydropyrimidine-5-carboxylate (0.57 g, 1 mmol) was reacted with 2-(morpholin-2-yl)acetic acid hydrochloride (0.3 g, 1.65 mmol) according to the procedure as described in Example 1, Step C to give the title compound as a yellow solid (0.34 g, 53%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-e62762c6edf049f6b0fcf4492c5b7d78
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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