Ethyl Acetoacetate → Ethyl 4-(5-fluoro-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-6-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524636Notes

Reaction equation

HRID 524636 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=2)[C:5]([CH:22]=O)=[CH:4][CH:3]=1.Cl.[S:25]1[CH:29]=[CH:28][N:27]=[C:26]1[C:30](=[NH:32])[NH2:31].O=[C:34]([CH3:41])[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:22]2[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:34]([CH3:41])[NH:31][C:30]([C:26]3[S:25][CH:29]=[CH:28][N:27]=3)=[N:32]2)=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 186795841,3-Thiazole-2-carboximidamide hydrochlorideHCID 1181075485-Fluoro-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-2-carbaldehyde

Product 1

HCID 118107590Ethyl 4-(5-fluoro-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-6-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 26%

Procedure

5-fluoro-3′,5′-bis(trifluoromethyl)-[1,1′-biphenyl]-2-carbaldehyde (2.34 g, 6.96 mmol) was reacted with thiazole-2-carboximidamide hydrochloride (1.14 g, 6.96 mmol) and ethyl 3-oxobutanoate (1.1 g, 8.35 mmol) according to the procedure as described in Example 1, Step A to give the title compound as a yellow solid (1 g, 26%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-e1c714fa54394ee99195a31878898a02
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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