Hydrochloric Acid → Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMate

HRID 1969170Notes

Reaction equation

[CH3:1][O-:2].[Na+].Br[N:5]1[C:9](=[O:10])CCC1=O.[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[C:22](C(N)=O)=[CH:21][N:20]=2)[CH2:15][CH2:14]1.Cl>CO.ClCCl>[CH3:1][O:2][C:9](=[O:10])[NH:5][C:22]1[CH:21]=[N:20][C:19]([N:16]2[CH2:15][CH2:14][N:13]([CH3:12])[CH2:18][CH2:17]2)=[CH:27][C:26]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34]

Participants

Conditions

Temperature: -5 °C

Procedure

2.15 ml (11.6 mMol) Sodium methoxide in methanol were added over 30 minutes to a suspension of 0.85 g (4.6 mMol) N-bromosuccinimide in 5.0 ml dichloromethane cooled to −5° C. The reaction mixture was stirred 16 hours at −5° C. Still at this temperature, a solution of 1.0 g (3.1 mMol) 6-(4-methyl-piperazin-1-yl)-4-o-tolyl-nicotinamide in 5.0 ml methanol was added over 20 minutes and stirred for 5 hours. 7.1 ml (7.1 mMol) Aqueous HCl 1N and 20 ml dichloromethane were added. The phases were separated and the organic phase was washed with deionized water. The aqueous phases were extracted with dichloromethane, brought to pH=8 with aqueous NaOH 1N and further extracted with dichloromethane. The latter organic extracts were combined, dried (Na2SO4) and concentrated to yield 1.08 g (quant.) [6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-carbamic acid methyl ester as a grey foam. MS (ISP): 341 (M+H+, 100), 284 (35).

Workup

stirringstirred for 5 hours
customThe phases were separated
washthe organic phase was washed with deionized water
extractionThe aqueous phases were extracted with dichloromethane
extractionfurther extracted with dichloromethane
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-3190c87e087349a6a10c125612ab4ef9
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426450B1

Reaction notes

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