Pyridine → HCID 178463990, compound

HRID 2121360Notes

Reaction equation

HRID 2121360 reaction equation
CN(C)C=O.[N:6]1[CH:11]=[CH:10]C=[CH:8][CH:7]=1.[C:12]([N:19]1[CH:23]=[CH:22]N=C1)([N:14]1[CH:18]=[CH:17]N=C1)=O.[NH2:24][C:25]1[C:33]([NH2:34])=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([NH2:29])=[O:28].[CH3:35]N(C)C=O.N1C=C[CH:43]=[CH:42][CH:41]=1>CC(C)=O.C(OCC)C>[CH2:11]([N:6]([CH2:35][CH2:22][CH2:23][NH:19][C:12]1[CH:41]=[C:42]([C:43]2[NH:24][C:25]3[C:26]([C:27]([NH2:29])=[O:28])=[CH:30][CH:31]=[CH:32][C:33]=3[N:34]=2)[CH:17]=[CH:18][N:14]=1)[CH2:7][CH3:8])[CH3:10]

Participants

8

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 104870292,3-DiaminobenzamideHCID 21954950Dimethylformamide pyridine

Product 1

HCID 178463990HCID 178463990, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

0.36 g (1.25 mmol) of product 24b was introduced into 10 ml of a mixture of dimethylformamide and pyridine (1:1) and stirred for 15 minutes. After addition of 0.21 g (1.31 mmol) of carbonyldiimidazole, the reaction mixture was stirred at room temp. for 1 hour. A solution of 0.28 g (1.25 mmol) of 2,3-diaminobenzamide in 5 ml of dimethylformamide/pyridine was then added. The reaction mixture was stirred at 50° C. for 2 hours. The residue after concentration of the reaction mixture in vacuo was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was separated off, dried over magnesium sulfate and concentrated in vacuo. The residue was stirred in 20 ml of glacial acetic acid at 100° C. for 1 hour. The residue after concentration of the reaction mixture in vacuo was purified by flash chromatography (toluene/tetrahydrofuran/methanol, 4/1/1+2.5% triethylamine). The product obtained in this way was dissolved in a little acetone. The precipitate obtained with diethyl ether was separated off and dried at 40° C. in vacuo. 0.22 g of yellow powder was obtained.

Workup

  1. stirringthe reaction mixture was stirred at room temp. for 1 hour
  2. stirringThe reaction mixture was stirred at 50° C. for 2 hours
  3. customThe residue after concentration of the reaction mixture in vacuo was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. customThe organic phase was separated off
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. stirringThe residue was stirred in 20 ml of glacial acetic acid at 100° C. for 1 hour
  8. customThe residue after concentration of the reaction mixture in vacuo was purified by flash chromatography (toluene/tetrahydrofuran/methanol, 4/1/1+2.5% triethylamine)
  9. customThe product obtained in this way
  10. customwas separated off
  11. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-2c7cca2036b448c1999bc59fa96f14b8
Source dataset
uspto-grants-2004_02
Patent number
US06696437B1

Reaction notes

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