(S)-morpholine-3-carboxylic acid → (3S)-4-((5-(ethoxycarbonyl)-6-(5-fluoro-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxyli c acid

HRID 524634Notes

Reaction equation

HRID 524634 reaction equation
Br[CH2:2][C:3]1[NH:8][C:7]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[N:6][CH:5]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[C:4]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][C@H:37]1[C:42]([OH:44])=[O:43]>>[CH2:34]([O:33][C:31]([C:4]1[CH:5]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=2)[N:6]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[NH:8][C:3]=1[CH2:2][N:36]1[CH2:41][CH2:40][O:39][CH2:38][C@H:37]1[C:42]([OH:44])=[O:43])=[O:32])[CH3:35]

Participants

3

Reactant 2

HCID 1501894(S)-morpholine-3-carboxylic acidHCID 118107602HCID 118107602, compound

Product 1

HCID 73295974(3S)-4-((5-(ethoxycarbonyl)-6-(5-fluoro-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxyli c acidYield 50%

Procedure

Ethyl 6-(bromomethyl)-4-(5-fluoro-4′-(trifluoromethyl)-[1,1′-biphenyl]-2-yl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (3 g, 5.3 mmol) was reacted with (S)-morpholine-3-carboxylic acid (0.69 g, 5.3 mmol) according to the procedure as described in Example 1, Step C to give the title compound as a yellow solid (1.64 g, 50%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-22f00e607e8e44fd86ea8fe20afca747
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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