3-Methylbenzeneethanol → 2-[2-Fluoro-4-methoxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid

HRID 521529Notes

Reaction equation

HRID 521529 reaction equation
CO[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([OH:12])[C:5]=1[F:13].[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22]O)[CH:16]=1.Cl.C[O:27][C:28]([C:30]1([NH2:39])[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31]1)=[O:29]>>[F:13][C:5]1[C:6]([O:12][CH2:22][CH2:21][C:17]2[CH:16]=[C:15]([CH3:24])[CH:20]=[CH:19][CH:18]=2)=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[C:3]([NH:39][C:30]1([C:28]([OH:29])=[O:27])[CH2:31][C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:38]1)=[O:14]

Participants

4

Reactant 3

HCID 746483-MethylbenzeneethanolHCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochlorideHCID 67076493Methyl 2-fluoro-3-hydroxy-4-methoxybenzoate

Product 1

HCID 670766632-[2-Fluoro-4-methoxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid

Procedure

2-Fluoro-3-hydroxy-4-methoxybenzoic acid methyl ester was etherified with 2-m-tolyl-ethanol in analogy to step 1 of example 1, the obtained ester hydrolyzed in analogy to example 2, the obtained carboxylic acid reacted with 2-amino-indane-2-carboxylic acid methyl ester hydrochloride in analogy to step 3 of example 1, and the methyl ester hydrolyzed in analogy to example 2.

Sources & evidence

ORD record
ord-6265f2aa74b14de69652b681af5b5ee3
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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