HCID 68455302, compound → HCID 11531816, compound

HRID 2356986Notes

Reaction equation

C(O[C:6](=O)[N:7]([CH:9]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]2[C:25]3[C:20](=[CH:21][C:22]([S:26]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=4)(=[O:28])=[O:27])=[CH:23][CH:24]=3)[O:19][CH2:18][CH2:17]2)[CH2:10]1)C)(C)(C)C>Cl.CCO>[F:35][C:31]1[CH:30]=[C:29]([S:26]([C:22]2[CH:21]=[C:20]3[C:25]([CH:16]([CH2:15][CH2:14][N:11]4[CH2:12][CH2:13][CH:9]([NH:7][CH3:6])[CH2:10]4)[CH2:17][CH2:18][O:19]3)=[CH:24][CH:23]=2)(=[O:28])=[O:27])[CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(1-{2-[7-(3-Fluoro-benzenesulfonyl)-chroman-4-yl]-ethyl}-pyrrolidin-3-yl)-methyl-carbamic acid tert-butyl ester (0.9 g) was dissolved in 2N HCl in EtOH (2 ml) and the mixture was heated at 60° C. for 40 minutes. The reaction mixture was cooled to room temperature and was quenched with saturated NaHCO3, extracted with methylene chloride, dried with MgSO4, filtered, concentrated and purified with preparative TLC (10% MeOH in methylene chloride with 1% Et3N) to give (1-{2-[7-(3-fluoro-benzenesulfonyl)-chroman-4-yl]-ethyl}-pyrrolidin-3-yl)-methyl-amine, which was treated with a few drops of 2N HCl in EtOH and dried under vacuum to give (1-{2-[7-(3-Fluoro-benzenesulfonyl)-chroman-4-yl]-ethyl}-pyrrolidin-3-yl)-methyl-amine HCl salt: 61.8 mg, MS: 419.5 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to room temperature
customwas quenched with saturated NaHCO3
extractionextracted with methylene chloride
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated
custompurified with preparative TLC (10% MeOH in methylene chloride with 1% Et3N)

Sources & evidence

ORD record: ord-e572558fe859458b898d01b442671a88
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759389B2

Reaction notes

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