Ethyl 4-chloroacetoacetate → {4-Methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid

HRID 1814159Notes

Reaction equation

HRID 1814159 reaction equation
COC1C=C(S)C=C(C)C=1.C(OC(=O)CC(=O)CCl)C.C([O:23][C:24](=[O:54])[CH2:25][C:26]1[C:27]2[C:34]([CH3:35])=[CH:33][C:32]([O:36][CH2:37][C:38]3[S:42][C:41]([C:43]4[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=4)=[N:40][C:39]=3[CH3:53])=[CH:31][C:28]=2[S:29][CH:30]=1)C>>[CH3:35][C:34]1[C:27]2[C:26]([CH2:25][C:24]([OH:54])=[O:23])=[CH:30][S:29][C:28]=2[CH:31]=[C:32]([O:36][CH2:37][C:38]2[S:42][C:41]([C:43]3[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:50])[F:51])=[CH:45][CH:44]=3)=[N:40][C:39]=2[CH3:53])[CH:33]=1

Participants

4

Reactant 3

HCID 69484Ethyl 4-chloroacetoacetateHCID 20770770{4-Methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid ethyl ester2×HCID 225047193-Methoxy-5-methylbenzenethiol

Product 1

HCID 22504735{4-Methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid

Procedure

The title compound was prepared in the manner analogous to example 5C starting with 3 3-methoxy-5-methyl-benzenethiol and the 4-chloro-3-oxo-butyric acid ethyl ester. MS m/z 251 (M+1). Step 2. Preparation of {4-Methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid ethyl ester (Compound 17B)

Sources & evidence

ORD record
ord-b36a98e385864681b4dcc6402b285275
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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