O-Phenylenediamine → HCID 18404103、化合物

HRID 1017712ノート

反応式

HRID 1017712 の反応式
C(O[C:4]([C:6]1[C:7](=[O:16])[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[N:11][CH:10]=2)=O)C.[C:17]1([NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23].C(=O)(O)[O-].[Na+]>>[NH:23]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:24]=[C:4]1[C:6]1[C:7](=[O:16])[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[N:11][CH:10]=2

参加物

4

反応物 3

HCID 7243O-PhenylenediamineHCID 516892Sodium BicarbonateHCID 12204015Ethyl 2-oxo-1,2-dihydro-1,7-naphthyridine-3-carboxylate

生成物 1

HCID 18404103HCID 18404103、化合物

反応条件

温度
200 °C

実験手順

A mixture of 6-3 (300 mg, 1.37 mmol, 1 equiv) and 1,2-phenylenediamine (223 mg, 2.06 mmol, 1.5 equiv) in polyphosphoric acid (8 mL) was heated at 200° C. for 3 h. The hot rxn mixture was poured into ice water (50 mL), and the resulting mixture was allowed to stand until all polyphosphoric acid had dissolved. The acidic suspension was neutralized with saturated aqueous sodium bicarbonate solution, then extracted with ethyl acetate (5×100 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (EtOAc) to afford 3-(1H-benzoimidazol-2-yl)-1H-[1,7]naphthyridine-2-one (6-4) as a yellow solid. 1H NMR (400 MHz, (CD3)2SO) δ 12.75 (s, 1H), 12.71 (s, 1H), 9.13 (s, 1H), 8.79 (s, 1H), 8.43 (d, 1H, J=5.2 Hz), 7.91 (d, 1H, J=5.2 Hz), 7.74 (m, 1H), 7.68 (m, 1H), 7.24 (m, 2H). HRMS (electrospray FT/ICR) calculated for C15H11N4O [M+H]+ 263.0933, found 263.0930.

後処理

  1. dissolutionhad dissolved
  2. extractionextracted with ethyl acetate (5×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (EtOAc)

出典と根拠

ORDレコード
ord-e95e358753924c34833ee96b0a2fafc9
出典データセット
uspto-grants-2002_11
特許番号
US06479512B1

反応ノート

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