Ethyl Acetate → HCID 46929262、化合物

HRID 1801490ノート

反応式

HRID 1801490 の反応式
CN(/[CH:4]=[C:5]1/[C:6](=O)[C:7]2[CH:19]=[CH:18][CH:17]=[N:16][C:8]=2[NH:9][C:10]2[CH:15]=[N:14][CH:13]=[CH:12][C:11]/1=2)C.[Cl-].[Cl:22][C:23]1[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=1)[CH2:26][NH:27][C:28]([NH2:30])=[NH2+:29].[O-]CC.[Na+].C(OCC)(=O)C>C(O)C>[Cl:22][C:23]1[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=1)[CH2:26][NH:27][C:28]1[N:30]=[CH:4][C:5]2[C:11]3[CH:12]=[CH:13][N:14]=[CH:15][C:10]=3[NH:9][C:8]3[N:16]=[CH:17][CH:18]=[CH:19][C:7]=3[C:6]=2[N:29]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 2723922Sodium ethoxideHCID 59506317(E)-6-((dimethylamino)methylene)-6,11-dihydro-5H-dipyrido[2,3-b:4',3'-f]azepin-5-oneHCID 178512446HCID 178512446、化合物

生成物 1

HCID 46929262HCID 46929262、化合物収率 30.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of (E)-6-((dimethylamino)methylene)-6,11-dihydro-5H-dipyrido[2,3-b :4′,3′-f]azepin-5-one (0.303 g), 1-(3-chlorobenzyl)guanidinium chloride (0.500 g) and sodium ethoxide (21% solution in ethanol) (0.5 mL) in absolute ethanol (15 mL) was refluxed in for 3 hours. The reaction mixture was cooled to room temperature and poured into ethyl acetate (150 mL), washed with water (200 mL), dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure to yield a brown solid. The crude product was purified by flash chromatography (SiO2, gradient 100% ethyl acetate to 5% methanol in dichloromethane) to give the pure desired product, N-(3-chlorobenzyl)-9H-dipyrido[2,3-b:4′,3′-f]pyrimido[4,5-d]azepin-2-amine as a bright yellow solid (0.134 g). M.p.=195-196° C.; 1H NMR (DMSO-d6) 400 MHz δ 8.46-8.07 (m, 7H), 7.42-7.28 (m, 4H), 7.09 (brs, 1H), 4.58 (s, 2H); LCMS (M+H)=387.

後処理

  1. temperaturewas refluxed in for 3 hours
  2. washwashed with water (200 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customto yield a brown solid
  6. customThe crude product was purified by flash chromatography (SiO2, gradient 100% ethyl acetate to 5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-64eeb4d55ae84249a2c356f76c39d472
出典データセット
uspto-grants-2013_01
特許番号
US08349827B2

反応ノート

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