4-amino-N-(2-chloro-3-pyridinyl)-1-methyl-1H-pyrazole-5-carboxamide → 1-Methyl-1,4,9,10-tetrahydro-pyrazolo[4,3-e]pyrido[3,2-b][1,4]diazepin-10-one

HRID 1702442Notes

Reaction equation

HRID 1702442 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:17])[C:6]=1[C:7]([NH:9][C:10]1[C:11](Cl)=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8]>S1(CCCC1)(=O)=O.S(=O)(=O)(O)O>[CH3:17][N:5]1[C:6]2[C:7](=[O:8])[NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[N:12][C:11]=3[NH:1][C:2]=2[CH:3]=[N:4]1

Participants

4

Reactant 1

HCID 205038164-amino-N-(2-chloro-3-pyridinyl)-1-methyl-1H-pyrazole-5-carboxamide

Product 1

HCID 205038231-Methyl-1,4,9,10-tetrahydro-pyrazolo[4,3-e]pyrido[3,2-b][1,4]diazepin-10-one

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 31347SulfolaneSolvent

Procedure

An amount of 25.0 gm (0.099 mol) of 4-amino-N-(2-chloro-3-pyridinyl)-1-methyl-1H-pyrazole-5-carboxamide was dissolved in 100 ml of sulfolane and, after addition of 5 drops of concentrated sulfuric acid, heated for 1 hour to 120° C. The cold reaction mixture was filtered, and the filtration residue was suspended with 5% aqueous ammonia solution and again filtered. The product obtained was thoroughly washed with water, stirred with methanol, and subjected to cold suction filtration. After drying, 14.6 gm (68.5% of theory) of colorless crystals were obtained (m.p.: 304°-305° C.).

Workup

  1. temperatureheated for 1 hour to 120° C
  2. customThe cold reaction mixture
  3. filtrationwas filtered
  4. filtrationagain filtered
  5. customThe product obtained
  6. washwas thoroughly washed with water
  7. filtrationsubjected to cold suction filtration
  8. customAfter drying
  9. custom14.6 gm (68.5% of theory) of colorless crystals were obtained (m.p.: 304°-305° C.)

Sources & evidence

ORD record
ord-9a440eab2ca0430a9f8a1bc567820e98
Source dataset
uspto-grants-1983_04
Patent number
US04381303

Reaction notes

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