4-Chlorobenzoyl chloride → HCID 58372843, compound

HRID 656742Notes

Reaction equation

HRID 656742 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[CH2:22][S:23][C:24]2[S:25][C:26]([CH3:29])=[N:27][N:28]=2)[CH:7]=1)[CH3:2].[Cl:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1>>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:36](=[O:37])[C:35]3[CH:39]=[CH:40][C:32]([Cl:31])=[CH:33][CH:34]=3)=[CH:17][C:16]=2[CH2:22][S:23][C:24]2[S:25][C:26]([CH3:29])=[N:27][N:28]=2)[CH:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 58372835HCID 58372835, compound

Product 1

HCID 58372843HCID 58372843, compound

Procedure

As described for Example 10, [3-(2-bromomethyl-4-nitro-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester and 5-methyl-1,3,4-thiadiazole-2-thiol were reacted to form {4-methoxy-3-[2-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-4-nitro-phenoxy]-phenyl}-acetic acid ethyl ester, which was reduced to {3-[4-amino-2-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid ethyl ester and then treated with 4-chlorobenzoyl chloride to provide {3-[4-(4-chloro-benzoylamino)-2-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid ethyl ester. Hydrolysis of the ester to the acid provided Compound 19.

Sources & evidence

ORD record
ord-b55fe7847a7d425b876915c9f22757f7
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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