Hydrochloric Acid → HCID 178441516, compound

HRID 1655457Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=2[N+:33]([O-])=O)[C:17](=O)[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11][CH:10]=1)#[N:2].[N-:36]=[N+:37]=[N-:38].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C.O>[CH2:18]([C:17]1[N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]3[NH:2][N:38]=[N:37][N:36]=3)=[CH:14][CH:13]=2)[C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=2[N:33]=1)[CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of methyl 4-[N-(2'-cyanobiphenyl-4-yl)methyl-N-valerylamino]-3-nitrobenzoate (1.7 g), sodium azide (3.9 g) and ammonium chloride (3.2 g) in DMF (17 ml) was stirred at 115 ° C. for 5 days. To the reaction mixture was added water and the mixture was neutralized with 1N-HCl, followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated to dryness. The concentrate was purified by column chromatography on silica gel to give crude crystals. Recrystallization from ethyl acetate gave colorless needles (0.67 g, 34%), m.p. 134-136° C.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water
customdried
concentrationconcentrated to dryness
customThe concentrate was purified by column chromatography on silica gel
customto give crude crystals
customRecrystallization from ethyl acetate

Sources & evidence

ORD record: ord-24f6b523307440d3b03ab85df22d2c98
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05250554

Reaction notes

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