Water → HCID 69183112, compound

HRID 2113597Notes

Reaction equation

HRID 2113597 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][N:19]=2)[N:16]=[CH:15][C:14]([C:20]#[N:21])=[C:13]3[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=2)[CH2:3][CH2:2]1.O.O.Cl[Sn]Cl.O.C(=O)(O)[O-].[Na+]>C(O)C.ClCCl.CO>[NH2:29][C:25]1[CH:24]=[C:23]([NH:22][C:13]2[C:12]3[C:17](=[CH:18][N:19]=[C:10]([NH:9][CH2:8][CH2:7][N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)[CH:11]=3)[N:16]=[CH:15][C:14]=2[C:20]#[N:21])[CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 69182742HCID 69182742, compound

Product 1

HCID 69183112HCID 69183112, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-(2-morpholinoethylamino)-4-(3-nitrophenylamino)-1,7-naphthyridine-3-carbonitrile (120 mg, 0.29 mmol, 1 eq) and SnCl2.2H2O (348 mg, 1.54 mmol, 5.3 eq) in ethyl alcohol (12 mL) was heated to reflux for 2.5 hr. After cooling to room temperature, water (10 mL) was added followed by sodium bicarbonate (500 mg). The mixture was stirred at room temperature for 1 hr. Ethyl acetate extraction followed by column chromatography (3-5% methyl alcohol in dichloromethane) yield 43 mg product (39% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 2.40-2.48 (m, 4 H) 2.53-2.60 (m, 2 H) 3.34-3.40 (m, 2 H) 3.54-3.63 (m, 4 H) 5.18-5.27 (m, 2 H) 6.39-6.47 (m, 3 H) 6.57 (s, 1 H) 7.01-7.08 (m, 2 H) 8.22 (s, 1 H) 8.81 (s, 1 H) 9.43 (s, 1 H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 hr
  3. extractionEthyl acetate extraction

Sources & evidence

ORD record
ord-c340205f3051412d8e1ff004bd665797
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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