Hydrochloric Acid → HCID 11460753, compound

HRID 229363Notes

Reaction equation

C[N:2]1[C:6]([CH3:7])=[N:5][C:4]([C:8]2[CH:13]=[CH:12][N:11]3[CH:14]=[C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])[N:16]=[C:10]3[CH:9]=2)=[N:3]1.Cl.N([O-])=O.[Na+].N[C:29](N)=O.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[CH3:29][N:3]1[C:4]([C:8]2[CH:13]=[CH:12][N:11]3[CH:14]=[C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])[N:16]=[C:10]3[CH:9]=2)=[N:5][C:6]([CH3:7])=[N:2]1

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of finely powdered amine (5) (4.00 g, 0.014 mol) and 4 N hydrogen chloride (400 mL) was stirred vigorously at 23° C. for 30 min, by which time the hydrochloride salt had precipitated out as a yellow solid. The mixture was cooled to 5° C. and a solution of sodium nitrite (1.46 g, 0.021 mol) in water (5 mL) was added drop wise. The mixture was stirred at this temperature for 30 min, then urea (0.59 g, 9.91 mmol) was added. The mixture was stirred at 23° C. for a further 1 h, then basified by portion wise addition of solid sodium bicarbonate. ethyl acetate was added and the mixture was stirred vigorously for 30 min, then filtered through Celite to remove insoluble black material. The ethyl acetate layer was worked up, adsorbed onto silica and chromatographed. Ethyl acetate eluted foreruns, while ethyl acetate/methanol (95:5) gave the chloride (6) as a solid (1.21 g). APCI-MS Found: [M+H]+=304, 302.

Workup

customhad precipitated out as a yellow solid
stirringThe mixture was stirred at 23° C. for a further 1 h
stirringthe mixture was stirred vigorously for 30 min
filtrationfiltered through Celite
customto remove insoluble black material
customchromatographed

Sources & evidence

ORD record: ord-1f309bb319fb4593b887e3e1f58e9afc
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563788B2

Reaction notes

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