HCID 10686342, compound → HCID 19377759, compound

HRID 2210894Notes

Reaction equation

HRID 2210894 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7]2[C:8]([N+:17]([O-])=O)=[C:9]3[CH2:16][O:15][CH2:14][CH2:13][C:10]3=[N:11][CH:12]=2)=[N:2]1.ClC(Cl)(Cl)C(NC1C=[N+]([O-])C2CCCCC=2C=1)=O>CO.[C].[Pd]>[NH2:17][C:8]1[C:7]([NH:6][C:3]2[CH:4]=[CH:5][O:1][N:2]=2)=[CH:12][N:11]=[C:10]2[CH2:13][CH2:14][O:15][CH2:16][C:9]=12

Participants

5

Reactant 2

HCID 10686342HCID 10686342, compoundHCID 19377776HCID 19377776, compound

Product 1

HCID 19377759HCID 19377759, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 435 mg of Compound 7 obtained in (3) above in 95% aqueous methanol is added 10% palladium carbon (40 mg) as catalyst, and the resultant mixture is hydrogenated at ordinary temperature under atmospheric pressure. The reaction mixture is filtered, and the hardly soluble solid is washed out with dimethylformamide. The filtrate is concentrated in vacuo, and the residue is recrystallized from methanol-methylene chloride to give 280 mg of the titled compound (II2b) as light brown crystals. Yield: 72% mp.: 209° to 211° C. Elemental Analysis (%) C12H12N4O3Calculated: C, 55.38; H, 4.65; N, 21.53 Found: C, 55.08; H, 4.54; N, 21.24 NMR (d6 -DMSO) δ: 2.73 (2H, t); 3.90 (2H, t); 4.51 (2H, s); 5.93 (2H, s, NH); 7.06 (1H, d); 7.93 (1H, s); 9.15 (1H, d); 10.07 (1H, s, NH)

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe hardly soluble solid is washed out with dimethylformamide
  3. concentrationThe filtrate is concentrated in vacuo
  4. customthe residue is recrystallized from methanol-methylene chloride

Sources & evidence

ORD record
ord-4081b33b24054bdeb2d5f4c6a7a4d4f6
Source dataset
uspto-grants-1995_10
Patent number
US05461062

Reaction notes

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