Pyridine → 6-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazine

HRID 1870771노트

반응식

HRID 1870771 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([NH2:19])=O)=[CH:13][CH:12]=1)[CH2:9][CH3:10].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]#[N:19])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 186932416-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-pyridazine-3-carboxamide

생성물 1

HCID 226225146-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The phenol from the previous step (1.73 g, 4.9 mmol) in THF (30 ml) was treated with pyridine (0.82 ml, 0.82 g, 10.2 mmol) followed by trifluoroacetic anhydride (1.61 ml, 2.42 g, 11.5 mmol). The mixture turned dark green and was left overnight at ambient temperature. The mixture was then evaporated to a gum, treated with an excess of an aqueous solution of sodium bicarbonate and stirred at ambient temperature for approximately 30 minutes. The resultant red solid was filtered, washed with water and sucked dry (1.8 g) and purified by MPLC to give 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-3-cyanopyridazine (as a white solid (0.87 g, 53%).

후처리

  1. customThe mixture was then evaporated to a gum
  2. additiontreated with an excess of an aqueous solution of sodium bicarbonate
  3. filtrationThe resultant red solid was filtered
  4. washwashed with water
  5. customsucked dry (1.8 g)
  6. custompurified by MPLC

출처 및 근거

ORD 기록
ord-32b819612ff54f16a31f323145559fb9
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100258

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