3,4-Diaminopyridine → HCID 178514937, compound

HRID 1663314Notes

Reaction equation

HRID 1663314 reaction equation
N1C=CC(N)=C(N)C=1.O=C1C2C(=CC=CC=2)C(=O)N1CCCCC(O)=O.[N:27]1[C:35]2[CH:34]=[CH:33][N:32]=[CH:31][C:30]=2[NH:29][C:28]=1[CH2:36][CH2:37][CH2:38][CH2:39][N:40]1[C:48](=[O:49])[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:41]1=O>O>[N:27]1[C:35]2[CH:34]=[CH:33][N:32]=[CH:31][C:30]=2[NH:29][C:28]=1[C:36]1[CH2:37][CH2:38][CH2:39][N:40]2[C:48](=[O:49])[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:41]=12

Participants

5

Reactant 3

HCID 59183,4-DiaminopyridineHCID 17149185-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)pentanoic acidHCID 669101862-{4-(3H-imidazo[4,5-c]pyridin-2-yl)butyl}isoindole-1,3-dione

Product 1

HCID 178514937HCID 178514937, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
210 °C

Procedure

4 g of pyridine-3,4-diamine and 9.5 g of 5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid are introduced into a 250 ml round-bottomed flask, followed by 45 g of polyphosphoric acid (PPA). The solid mixture is heated to 210° C. in an oil bath. During the reaction, the transient formation of 2-{4-(3H-imidazo[4,5-c]pyridin-2-yl)butyl}isoindole-1,3-dione is noted. After heating for 16 hours, the reaction is complete. After cooling, the reaction mixture is taken up in water. The impurities are eliminated by extraction with ethyl acetate. The aqueous phase is neutralized (pH 7) with 2N sodium hydroxide. The product is recovered after 6 successive extractions with a mixture of ethyl acetate and methanol (9/1 by volume). After purification by flash chromatography silica, elution being carried out with a mixture of dichloromethane and methanol (95/5 by volume), 1.46 g of 1-{3-H-imidazo[4,5-c]pyridin-2-yl}-3,4-dihydro-2H-pyrido[2,1-a]isoindole-6-one are obtained in the form of a white solid, the characteristics of which are as follows:

Workup

  1. customDuring the reaction
  2. temperatureAfter heating for 16 hours
  3. temperatureAfter cooling
  4. extractionThe impurities are eliminated by extraction with ethyl acetate
  5. customThe product is recovered
  6. extractionafter 6 successive extractions
  7. additionwith a mixture of ethyl acetate and methanol (9/1 by volume)
  8. customAfter purification
  9. washby flash chromatography silica, elution
  10. additionbeing carried out with a mixture of dichloromethane and methanol (95/5 by volume), 1.46 g of 1-{3-H-imidazo[4,5-c]pyridin-2-yl}-3,4-dihydro-2H-pyrido[2,1-a]isoindole-6-one
  11. customare obtained in the form of a white solid

Sources & evidence

ORD record
ord-5d5e8c0822f24100a10e5b80a9c04de6
Source dataset
uspto-grants-2011_10
Patent number
US08034939B2

Reaction notes

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