Benzenesulfonyl chloride → Sotirimod

HRID 2090173Notes

Reaction equation

[OH-].[NH4+:2].[CH3:3][C:4]1[N:5]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:6]2[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:9]([O-])=[CH:8][C:7]=2[N:17]=1.C1(S(Cl)(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C.O>[CH3:3][C:4]1[N:5]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:6]2[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:2])[C:7]=2[N:17]=1

Participants

Conditions

Temperature: 11 °C

Procedure

Aqueous ammonium hydroxide (5.07 kg of 30% w/w) was added over a period of ten minutes to a suspension of 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-5-oxide (6.00 kg, 23.4 mol) in ethanol (23.2 kg) at 22° C. The reaction was stirred for five minutes. Benzenesulfonyl chloride (8.80 kg, 49.8 mol) was added over a period of 30 minutes. The reaction was stirred for one hour at 22° C. A solution of aqueous sodium hydroxide (15.0 kg of 25% w/w) and water (34.0 kg) was added to the reaction mixture over a period of 30 minutes at 22° C. to adjust the mixture to pH 13. The resulting mixture was cooled to 11° C. and stirred at that temperature for three hours and then separated by centrifugation. A solid was collected, washed with demineralized water (105.0 kg) at 22° C. until the filtrate was pH 7, and dried under vacuum (2×103 Pa, 0.02 bar) at 45° C. for 24 hours to provide 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine.

Workup

stirringThe reaction was stirred for one hour at 22° C
stirringstirred at that temperature for three hours
customseparated by centrifugation
customA solid was collected
washwashed with demineralized water (105.0 kg) at 22° C. until the filtrate
customdried under vacuum (2×103 Pa, 0.02 bar) at 45° C. for 24 hours

Sources & evidence

ORD record: ord-249c49deffe443629129467228787bbf
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436176B2

Reaction notes

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