4-methyl-5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one hydrochloride → HCID 69087547, compound

HRID 2173436Notes

Reaction equation

HRID 2173436 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]3[CH:12]([C:15]([OH:17])=O)[CH2:13][CH2:14][C:8]=3[CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.Cl.[CH3:19][C:20]1[C:28]2[CH2:27][O:26][C:25](=[O:29])[C:24]=2[CH:23]=[CH:22][C:21]=1[CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[CH3:19][C:20]1[C:28]2[CH2:27][O:26][C:25](=[O:29])[C:24]=2[CH:23]=[CH:22][C:21]=1[CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][N:35]([C:15]([CH:12]2[C:9]3[CH:10]=[N:11][C:6]([N:1]4[CH:5]=[N:4][N:3]=[N:2]4)=[CH:7][C:8]=3[CH2:14][CH2:13]2)=[O:17])[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 675172294-methyl-5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one hydrochlorideHCID 675172303-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylic acid

Product 1

HCID 69087547HCID 69087547, compound

Procedure

4-Methyl-5-[2-(4-{[3-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl]carbonyl}piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one was prepared starting from 3-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylic acid and 4-methyl-5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one hydrochloride in an analogous fashion to that described by GENERAL METHOD B. The resulting mixture of two enantiomers was separated by preparative chiral SFC HPLC using a ChiralPak AD-H 250×30 mm I.D. column and eluting with A: SF CO2 and B: ethanol/acetonitrile (2:1) (0.1% DEA) with flow rate of 50 mL/min. The single title isomers were obtained.

Workup

  1. additionThe resulting mixture of two enantiomers
  2. customwas separated by preparative chiral SFC HPLC
  3. washcolumn and eluting with A: SF CO2 and B
  4. customThe single title isomers were obtained

Sources & evidence

ORD record
ord-7bc38ffb03b94de381aa49e84515a5a1
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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