Ethyl Acetate → HCID 46929262, 화합물

HRID 1801490노트

반응식

HRID 1801490 반응식
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

참가 물질

6

반응물 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, 화합물

생성물 1

HCID 46929262HCID 46929262, 화합물수율 30.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-64eeb4d55ae84249a2c356f76c39d472
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349827B2

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