Hydrochloric Acid → HCID 9945768, compound

HRID 2183540Notes

Reaction equation

[N:1](OCCCC)=O.[CH2:8]([CH:10]([NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([NH:21][C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])[C:15]=1[NH2:31])[CH2:11][CH3:12])[CH3:9].Cl.[OH-].[Na+]>C(#N)C>[CH2:8]([CH:10]([NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]2[N:21]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[CH3:30])[N:1]=[N:31][C:15]=12)[CH2:11][CH3:12])[CH3:9]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of butyl nitrite (119 mg, 1.15 mmol) and N4-(1-ethyl-propyl)-6-methyl-N2-(2,4,6-trimethyl-phenyl)-pyridine-2,3,4-triamine (250 mg, 0.766 mmol) in anhydrous acetonitrile (16 ml) was heated at 65° C. for 2 hours. The mixture was cooled to room temperature and 2N HCl (16 ml) was added. The mixture was neutralized with 2N NaOH and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give 250 mg of the crude product as a brown oil. The oil residue was purified through silica gel column using chloroform as eluent to give 201 mg of the title compound as golden yellow solid. Mp 131-133° C. 1H NMR (CDCl3) ä 7.022(s, 2H), 6.20(s, 1H), 5.44(d, 1H), 3.65(m, 1H), 2.50(s, 3H), 2.36(s, 3H), 1.96(s, 6H), 1.5-1.8(m, 4H), 1.03(t, 6H)ppm.

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
customdried
concentrationconcentrated
customto give 250 mg of the crude product as a brown oil
customThe oil residue was purified through silica gel column

Sources & evidence

ORD record: ord-76926b197de54a59b38ad1becac31ca8
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900217B2

Reaction notes

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