Triethylamine → 8-Methyl-6-(1,2,5,6-tetrahydropyridin-1-yl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 1492399

反応式

HRID 1492399 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[N:7]=1.[NH:12]1[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]1.C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[CH3:11][C:4]1[C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[N:7]=[C:2]([N:12]2[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]2)[CH:3]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 127501,2,3,6-TetrahydropyridineHCID 40531136-Chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazine

生成物 1

HCID 189505468-Methyl-6-(1,2,5,6-tetrahydropyridin-1-yl)-1,2,4-triazolo[4,3-b]pyridazine

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 84.3 g of 6-chloro-8-methyl-1,2,4-triazolo [4,3-b]pyridazine, 62.4 g of 1,2,5,6-tetrahydropyridine and 101 g of triethylamine in one liter of ethanol was refluxed under nitrogen for 21 hours. The bulk of the solvent was removed at the rotary evaporator. The residual semi-solid was dissolved in 1000 ml of dichloromethane and washed with 500 ml of saturated sodium bicarbonate solution. The aqueous layer was back washed with fresh dichloromethane (2×200 ml) and the combined organic layers were dried over anhydrous sodium sulfate. Evaporation of the solvent gave a light-brown oil which slowly solidified. This was taken up in 230 ml of hot ethyl acetate and cooled. After cooling the mixture slowly to room temperature and then to 5° C., the cream colored needles which formed were collected, washed with ethyl ether/ethyl acetate (2/1) then with ethyl ether and dried to give 8-methyl-6-(1,2,5,6-tetrahydropyridin-1-yl)-1,2,4-triazolo-[4,3-b]pyridazine melting at about 103°-106° C.

後処理

  1. customThe bulk of the solvent was removed at the rotary evaporator
  2. dissolutionThe residual semi-solid was dissolved in 1000 ml of dichloromethane
  3. washwashed with 500 ml of saturated sodium bicarbonate solution
  4. washThe aqueous layer was back washed with fresh dichloromethane (2×200 ml)
  5. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  6. customEvaporation of the solvent
  7. customgave a light-brown oil which
  8. temperaturecooled
  9. customto 5° C., the cream colored needles which formed
  10. customwere collected
  11. washwashed with ethyl ether/ethyl acetate (2/1)
  12. dry with materialwith ethyl ether and dried

出典と根拠

ORDレコード
ord-c4c7a1cf14d44c9eb6e34472a8e25fb5
出典データセット
uspto-grants-1994_12
特許番号
US05374632

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