3-Methylbenzeneethanol → 2-{[5-Acetyl-4-(2-m-tolyl-ethoxy)-thiophene-2-carbonyl]-amino}-indane-2-carboxylic acid

HRID 1810854Notes

Reaction equation

HRID 1810854 reaction equation
CO[C:3]([C:5]1[S:6][C:7]([C:11](=[O:13])[CH3:12])=[C:8]([OH:10])[CH:9]=1)=[O:4].[CH3:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22]O)[CH:18]=[CH:19][CH:20]=1.Cl.C[O:26][C:27]([C:29]1([NH2:38])[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1)=[O:28]>>[C:11]([C:7]1[S:6][C:5]([C:3]([NH:38][C:29]2([C:27]([OH:28])=[O:26])[CH2:30][C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:37]2)=[O:4])=[CH:9][C:8]=1[O:10][CH2:22][CH2:21][C:17]1[CH:16]=[C:15]([CH3:14])[CH:20]=[CH:19][CH:18]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 746483-MethylbenzeneethanolHCID 106080802-Thiophenecarboxylic acid, 5-acetyl-4-hydroxy-, methyl esterHCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochloride

Product 1

HCID 444821442-{[5-Acetyl-4-(2-m-tolyl-ethoxy)-thiophene-2-carbonyl]-amino}-indane-2-carboxylic acid

Procedure

The title compound was synthesized by reaction of 5-acetyl-4-hydroxy-thiophene-2-carboxylic acid methyl ester with 2-(3-methylphenyl)-ethanol in analogy to step 1 of example 1, subsequent ester hydrolysis in analogy to example 2, reaction with 2-amino-indane-2-carboxylic acid methyl ester hydrochloride in analogy to step 1 of example 15, and ester hydrolysis in analogy to example 2.

Sources & evidence

ORD record
ord-e6a4ec6d8cd24edd81e2458f03067179
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

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