Hydrochloric Acid → HCID 178515831, compound

HRID 1742287Notes

Reaction equation

HRID 1742287 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:10](=[O:11])[CH:9]=[CH:8][C:7]([C:12]2[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:14][N:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=23)=[N:6]1)#[N:2].[N-:27]=[N+:28]=[N-:29].[Na+].Cl.C(N(CC)CC)C.Cl>CN1CCCC1=O.O>[NH:27]1[C:1]([CH2:3][CH2:4][N:5]2[C:10](=[O:11])[CH:9]=[CH:8][C:7]([C:12]3[C:13]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[N:14][N:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=34)=[N:6]2)=[N:2][N:29]=[N:28]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 19009017HCID 19009017, compound

Product 1

HCID 178515831HCID 178515831, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-[2-(2-cyanoethyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.35 g), sodium azide (0.20 g) and triethylamine hydrochloride (0.21 g) in N-methylpyrrolidone (10 ml) was stirred at 150° C. for 4 hours under nitrogen atmosphere. The reaction mixture was poured into water (30 ml), acidified with 10% hydrochloric acid (5 ml), and extracted twice with ethyl acetate. The combined extracts were washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of chloroform and methanol (20:1) as an eluent. The fractions containing the object compound were combined and evaporated in vacuo. The residue was recrystallized from ethyl acetate to give 3-[2-{2-(1H-tetrazol-5-yl)ethyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.06 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of chloroform and methanol (20:1) as an eluent
  7. additionThe fractions containing the object compound
  8. customevaporated in vacuo
  9. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-41f581fce68c4633a37b0eaa51095696
Source dataset
uspto-grants-1994_08
Patent number
US05338743

Reaction notes

Loading…