Ethyl 3-oxo-3-(1,3-thiazol-2-ylamino)propanoate → Ethyl 2-[(2-chloro-1-oxo-3,3-dimethylbutyl)-amino]-beta-oxo-alpha-[(2-thiazolylamino)-carbonyl]-3-(trifluoromethyl)-benzene-propanoate

HRID 1789219Notes

Reaction equation

HRID 1789219 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[Cl:15][CH:16]([C:21]1[O:26][C:25](=[O:27])[C:24]2[CH:28]=[CH:29][CH:30]=[C:31]([C:32]([F:35])([F:34])[F:33])[C:23]=2[N:22]=1)[C:17]([CH3:20])([CH3:19])[CH3:18]>>[Cl:15][CH:16]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:21]([NH:22][C:23]1[C:31]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](=[O:27])[CH:8]([C:7]([NH:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:26]

Participants

3

Reactant 2

HCID 7339584Ethyl 3-oxo-3-(1,3-thiazol-2-ylamino)propanoateHCID 141405842-(1-chloro-2,2-dimethylpropyl)-8-trifluoromethyl-4H-3,1-benzoxazine-4-one

Product 1

HCID 20188955Ethyl 2-[(2-chloro-1-oxo-3,3-dimethylbutyl)-amino]-beta-oxo-alpha-[(2-thiazolylamino)-carbonyl]-3-(trifluoromethyl)-benzene-propanoateYield 88.5%

Procedure

Using the procedure of Step A of Example 4, 7.7 g of ethyl 3-(2-thiazolylamino)-3-oxo-propanoate and 10.55 g of 2-(1-chloro-2,2-dimethylpropyl)-8-trifluoromethyl-4H-3,1-benzoxazine-4-one [prepared according to the process described in the European Pat. No. 0040573] were reacted to obtain 15.6 g of ethyl 2-[(2-chloro-1-oxo-3,3-dimethylbutyl)-amino]-β-oxo-α-[(2-thiazolylamino)-carbonyl]-3-(trifluoromethyl)-benzene-propanoate melting at 180° C.

Workup

  1. customprepared
  2. custom0040573] were reacted

Sources & evidence

ORD record
ord-8157287710cc4674bb21ea720e6e9ab7
Source dataset
uspto-grants-1987_08
Patent number
US04687857

Reaction notes

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