Acetonitrile → HCID 131727400, compound

HRID 2110161Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[S:14](Cl)(=[O:16])=[O:15])[CH2:6]1)=[O:4].[Br:18][C:19]1[CH:20]=[C:21]([N:26]2[CH2:31][C@H:30]([CH3:32])[NH:29][C@H:28]([CH3:33])[CH2:27]2)[CH:22]=[CH:23][C:24]=1[Cl:25].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[Br:18][C:19]1[CH:20]=[C:21]([N:26]2[CH2:27][C@@H:28]([CH3:33])[N:29]([S:14]([C:11]3[CH:10]=[CH:9][CH:8]=[C:7]4[C:12]=3[CH2:13][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]4)(=[O:16])=[O:15])[C@@H:30]([CH3:32])[CH2:31]2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

Conditions

Temperature: 55 °C

Procedure

4-Chlorosulfonyl-indan-2(R,S)-carboxylic acid methyl ester (225 mg, 0.82 mmol) was added to a mixture of 1-(3-bromo-4-chlorophenyl)-cis-3,5-dimethylpiperazine (569 mg, 1.87 mmol), potassium carbonate (500 mg, 3.6 mmol), and acetonitrile (8 mL) at rt under nitrogen, and the reaction was heated at 55° C. for 3 h. After allowing the reaction to cool to rt, it was poured into water (40 mL) and extracted with dichloromethane (40 mL×2). The combined organic extracts were dried, filtered, concentrated, and purified by silica gel chromatography (9:1→3:1; hexanes:ethyl acetate) to give methyl 4-(4-(3-bromo-4-chlorophenyl)-cis-2,6-dimethylpiperazin-1-ylsulfonyl)-2,3-dihydro-1H-indene-2(R,S)-carboxylate: MS (ESI): 541.2 (M+H).

Workup

customthe reaction
temperatureto cool to rt
extractionextracted with dichloromethane (40 mL×2)
customThe combined organic extracts were dried
filtrationfiltered
concentrationconcentrated
custompurified by silica gel chromatography (9:1→3:1; hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-79da05b2dd8c469e8cf56ca52a6b29be
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517884B2

Reaction notes

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