2-Aminopyridine → HCID 57832788、化合物

HRID 729500ノート

反応式

HRID 729500 の反応式
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]

参加物

5

反応物 3

HCID 104392-AminopyridineHCID 743724-tert-Butylbenzoyl chlorideHCID 129098391,2-Diaminopyridinium iodide2 回

生成物 1

HCID 57832788HCID 57832788、化合物収率 74%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-058ca0d1d56e4ff79cacecd226266326
出典データセット
uspto-grants-2009_09
特許番号
US07582636B2

反応ノート

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