2-Aminopyridine → HCID 57832788, compound

HRID 729500Notes

Reaction equation

NC1C=CC=CN=1.[I-].[NH2:9][N+:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16].[C:17]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=O)=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>N1C=CC=CC=1>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([C:25]2[N:16]=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:28][CH:29]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 85 °C

Procedure

2-Aminopyridine was converted to 1,2-diaminopyridinium iodide from a known literature method (J. Org. Chem., 31:260-265 (1996)). 1,2-Diaminopyridinium iodide (0.270 g, 1.1 mmol) was treated with 4-tert-butyl-benzoyl chloride (0.432 g, 2.2 mmol) in pyridine (2 mL). The reaction was heated at 85° C. in a sealed tube for 3 h, at which time the mixture was cooled to room temperature. The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL). The ethyl acetate extract was dried over magnesium sulfate and concentrated. The crude material was purified by flash silica gel chromatography, eluting with 25% ethyl acetate/hexanes (Rf=0.4) to yield 0.205 g (74%) of the purified product. MS (ES) m/z 252.2; HPLC (Method B): r.t.=6.7 min., purity 100% at 210-370 nm, 100% at 254 nm. HRMS: calcd for C16H17N3+H+, 252.14952; found (ESI, [M+H]30 ), 252.149.

Workup

temperaturewas cooled to room temperature
customThe reaction was partitioned between ethyl acetate (50 mL) and water (50 mL)
extractionThe ethyl acetate extract
dry with materialwas dried over magnesium sulfate
concentrationconcentrated
customThe crude material was purified by flash silica gel chromatography
washeluting with 25% ethyl acetate/hexanes (Rf=0.4)

Sources & evidence

ORD record: ord-058ca0d1d56e4ff79cacecd226266326
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582636B2

Reaction notes

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