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

HRID 524638Notes

Reaction equation

HRID 524638 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]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[C:4]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36].[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][C@H:41]1[C:46]([OH:48])=[O:47]>>[CH2:38]([O:37][C:35]([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]=[C:23]([C:31]([F:32])([F:34])[F:33])[CH:24]=[C:25]([C:27]([F:29])([F:30])[F:28])[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:40]1[CH2:45][CH2:44][O:43][CH2:42][C@H:41]1[C:46]([OH:48])=[O:47])=[O:36])[CH3:39]

Participants

3

Reactant 2

HCID 1501894(S)-morpholine-3-carboxylic acidHCID 118107610Ethyl 6-(bromomethyl)-4-(5-fluoro-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107564(3S)-4-((5-(ethoxycarbonyl)-6-(5-fluoro-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acidYield 58%

Procedure

Ethyl 6-(bromomethyl)-4-(5-fluoro-3′,5′-bis(trifluoromethyl)-[1,1′-biphenyl]-2-yl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (3.37 g, 5.3 mmol) was reacted with (S)-morpholine-3-carboxylic acid (0.69 g, 5.3 mmol) according to the procedure described in Example 1, Step C to give the title compound as a yellow solid (2.11 g, 58%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-323cdfd358ec4f1a846ce118142550d4
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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