Ethyl Acetate → HCID 46929262, compound

HRID 1801490Notes

Reaction equation

HRID 1801490 reaction equation
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

Participants

6

Reactant 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, compound

Product 1

HCID 46929262HCID 46929262, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-64eeb4d55ae84249a2c356f76c39d472
Source dataset
uspto-grants-2013_01
Patent number
US08349827B2

Reaction notes

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