2-Aminopyridine → HCID 57832788, 화합물

HRID 729500노트

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HRID 729500 반응식
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]

참가 물질

5

반응물 3

HCID 104392-AminopyridineHCID 743724-tert-Butylbenzoyl chlorideHCID 129098391,2-Diaminopyridinium iodide2회

생성물 1

HCID 57832788HCID 57832788, 화합물수율 74%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
85 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-058ca0d1d56e4ff79cacecd226266326
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582636B2

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