(S)-4-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrimidine-2-carboxylic acid → (S)-4-(4-chlorophenyl)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrimidine-2-carboxamide

HRID 1528438Notes

Reaction equation

HRID 1528438 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=[C:10]([C:21]([OH:23])=O)[N:9]=2)=[CH:4][CH:3]=1.Cl.[F:25][C:26]([F:35])([F:34])[C:27]1[N:31]=[C:30]([CH2:32][NH2:33])[O:29][N:28]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][C@@H:15]([CH3:20])[C:16]([F:18])([F:17])[F:19])=[CH:12][N:11]=[C:10]([C:21]([NH:33][CH2:32][C:30]3[O:29][N:28]=[C:27]([C:26]([F:35])([F:34])[F:25])[N:31]=3)=[O:23])[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 66678696(S)-4-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrimidine-2-carboxylic acidHCID 66687518[3-(Trifluoromethyl)-1,2,4-oxadiazol-5-yl]methanamine hydrochloride

Product 1

HCID 56928595(S)-4-(4-chlorophenyl)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrimidine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 1, using (S)-4-(4-chlorophenyl)-5-(1,1,1-trifluoropropan-2-yloxy)pyrimidine-2-carboxylic acid (Example AQ) and C-(3-trifluoromethyl-[1,2,4]oxadiazol-5-yl)-methylamine hydrochloride (CAN 944905-93-5; example AK) as starting materials. MS: 496.1 (M+H)+.

Sources & evidence

ORD record
ord-17746f2622d348aa9810c2ae6c45e9b0
Source dataset
uspto-grants-2015_07
Patent number
US09090599B2

Reaction notes

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