3,4-Diaminopyridine → HCID 178462453, compound

HRID 497165Notes

Reaction equation

[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH:16]=O)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[NH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[NH2:25]>[N+](C1C=CC=CC=1)([O-])=O>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]3[NH:25][C:24]4[CH:23]=[CH:22][N:21]=[CH:20][C:19]=4[N:18]=3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

Conditions

Temperature: 145 °C

Procedure

A mixture of 9-ethyl-9H-carbazole-3-carbaldehyde (444 mg, 1.99 mmol) and 3,4-diaminopyridine (217 mg, 1.99 mmol) in nitrobenzene (1.5 ml) was heated at 145° C. for 24 hours. The reaction mixture was cooled to room temperature and purified directly by flash column chromatography (0.1% ammonium hydroxide/5% methanol/dichloromethane) to afford the title compound 5A (94 mg):

Workup

temperatureThe reaction mixture was cooled to room temperature
custompurified directly by flash column chromatography (0.1% ammonium hydroxide/5% methanol/dichloromethane)

Sources & evidence

ORD record: ord-67094657cd7240f7938c7e6bb2728f24
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949564B2

Reaction notes

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