2-Acetamidothiazole → 2-[(2-chloro-1-oxo-pentyl)-amino]-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene propanamide

HRID 648749Notes

Reaction equation

HRID 648749 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:9])[CH3:8].[Cl:10][CH:11]([C:15]1[O:20][C:19](=[O:21])[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26]([F:29])([F:28])[F:27])[C:17]=2[N:16]=1)[CH2:12][CH2:13][CH3:14]>O1CCCC1.C([Li])CCC.CCCCCC>[Cl:10][CH:11]([CH2:12][CH2:13][CH3:14])[C:15]([NH:16][C:17]1[C:25]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](=[O:21])[CH2:8][C:7]([NH:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[O:9])=[O:20]

Participants

5

Reactant 2

HCID 176252-AcetamidothiazoleHCID 134230804H-3,1-Benzoxazin-4-one, 2-(1-chlorobutyl)-8-(trifluoromethyl)-

Product 1

HCID 134230832-[(2-chloro-1-oxo-pentyl)-amino]-beta-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene propanamideYield 72.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418244HCID 178418244, compoundSolvent

Procedure

Using the procedure of Step A of Example 6, a solution of 6.94 g of N-(2-thiazolyl)-acetamide in 280 ml of tetrahydrofuran and 70 ml of a butyllithium-hexane solution and a solution of 7.8 g of the product of Step A in 40 ml of tetrahydrofuran were reacted to obtain 8.3 g of 2-[(2-chloro-1-oxo-pentyl)-amino]-β-oxo-N-(2-thiazolyl)-3-trifluoromethyl-benzene propanamide melting towards 184°-186° C.

Sources & evidence

ORD record
ord-3d8b06f518f645bca6badbec8e481246
Source dataset
uspto-grants-1988_04
Patent number
US04736033

Reaction notes

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