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

HRID 524719Notes

Reaction equation

HRID 524719 reaction equation
Br[CH2:2][C:3]1[NH:8][C:7]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:6][CH:5]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[Cl:23])[C:4]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].Cl.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH:31]1[CH2:36][C:37]([OH:39])=[O:38]>>[Cl:23][C:17]1[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=1[CH:5]1[N:6]=[C:7]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][N:10]=2)[NH:8][C:3]([CH2:2][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH:31]2[CH2:36][C:37]([OH:39])=[O:38])=[C:4]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

3

Reactant 2

HCID 130995762-(Morpholin-3-yl)acetic acid hydrochlorideHCID 118107538Ethyl 6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(3-fluoro pyridin-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 900425432-(4-((6-(2-Chloro-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(3-fluoropyridin-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholin-3-yl)acetic acidYield 48%

Procedure

Ethyl 6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(3-fluoropyridin-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.72 g, 1.53 mmol) was reacted with 2-(morpholin-3-yl)acetic acid hydrochloride (0.28 g, 1.53 mmol) according to the procedure as described in Example 1, Step C to give the title compound as a yellow solid (0.39 g, 48%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-672427b8c2b9497aa27d9a10dc420139
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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