Nitroethane → Tert-butyl (6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

HRID 40205

반응식

HRID 40205 반응식
[N+:1]([CH2:4][CH3:5])([O-:3])=O.C1(N=C=O)C=CC=CC=1.[C:15]([C:17]1[CH:18]=[CH:19][C:20]2[N:21]([C:23]([CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[N:24][N:25]=2)[N:22]=1)#[CH:16].C(N(CC)CC)C>C1C=CC=CC=1>[C:30]([O:29][C:28](=[O:34])[NH:27][CH2:26][C:23]1[N:21]2[N:22]=[C:17]([C:15]3[O:3][N:1]=[C:4]([CH3:5])[CH:16]=3)[CH:18]=[CH:19][C:20]2=[N:25][N:24]=1)([CH3:33])([CH3:32])[CH3:31]

참가 물질

6

반응물 4

HCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 57691050tert-Butyl (6-ethynyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

생성물 1

HCID 57691036Tert-butyl (6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
50 °C

실험 절차

To a solution of nitroethane (1.02 ml, 14.3 mmol) in benzene (50 mL) was added phenyl isocyanate (3.12 ml, 28.5 mmol). The mixture was stirred at 50° C. for twenty minutes followed by the addition of tert-butyl (6-ethynyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (3.00 g, 11.0 mmol) and triethylamine (0.0765 ml, 0.549 mmol). The mixture was stirred at 50° C. for six hours then at room temperature overnight. The mixture was cooled to room temperature, filtered and the resulting brown precipitate was washed with additional benzene. The filtrate was concentrated to yield the product as a black solid. MS m/z=331.1 [M+1]+. Calc'd for C15H18N6O3: 330.1.

후처리

  1. stirringThe mixture was stirred at 50° C. for six hours
  2. customat room temperature
  3. customovernight
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationfiltered
  6. washthe resulting brown precipitate was washed with additional benzene
  7. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-d952825d729b4d20be4a45b727aa6332
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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