HCID 22141253, compound → N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl)methanesulfonamide

HRID 428933Notes

Reaction equation

C([N:4]1[CH2:9][CH:8]2[CH:6]([C:7]2([C:11]2[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[CH3:10])[CH2:5]1)C=C>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][C:7]1([C:11]2[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[CH:8]2[CH:6]1[CH2:5][NH:4][CH2:9]2

Participants

Conditions

Temperature: 35 °C

Procedure

A stirred mixture of N-[3-(3-allyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Example 56, 1.90 g, 6.19 mmol), tetrakis(triphenylphosphine)palladium (0) (71.8 mg, 62.1 mmol) and N,N-dimethylbarbituric acid (2.91 g, 18.6 mmol) in dichloromethane (15 ml) was degassed and then heated to 35° C. under nitrogen for 3 h. The solution was rapidly stirred with aqueous hydrochloric acid solution (2M, 40 ml) and the aqueous portion was separated, this process was repeated. The combined aqueous layers were washed with dichloromethane (7×50 ml), and then concentrated in vacuo to give the hydrochloride salt of the title compound as an off white solid (1.40 g, 74%).

Workup

customwas degassed
customthe aqueous portion was separated
washThe combined aqueous layers were washed with dichloromethane (7×50 ml)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a2769deb2ad447fa823bd7fe9c3b9a30
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313312B1

Reaction notes

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