Acetic Acid → HCID 59716656, 화합물

HRID 2224225노트

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HRID 2224225 반응식
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][N:12]1[C:34](=[O:35])[N:15]2[N:16]=[CH:17][C:18]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[C:19]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[C:14]2=[N:13]1)(=O)C.O(C)[Na].C(O)(=O)C>CO>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][N:12]1[C:34](=[O:35])[N:15]2[N:16]=[CH:17][C:18]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[C:19]([C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[C:14]2=[N:13]1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 59716641HCID 59716641, 화합물2회HCID 178418582HCID 178418582, 화합물

생성물 1

HCID 59716656HCID 59716656, 화합물수율 79%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

2-((7,8-Bis(4-chlorophenyl)-3-oxo-[1,2,4]triazolo[4,3-b]pyridazin-2(3H)-yl)methyl)phenyl acetate, prepared as described in 25A, (1.13 g), was dissolved in 25 mL of CH3OH. A solution of NaOCH3 (121 mg, 2.24 mmol) in a small amount of CH3OH (2 mL) was added to the reaction, and then, the reaction was stirred overnight. After this time, 0.3 mL of acetic acid was added to the reaction. The reaction was stirred for an additional 10 min, and then the resultant solution was concentrated under reduced pressure. The crude residue was purified using silica gel column chromatography using an automated system, eluting with a gradient of 0% to 60% EtOAc/hexanes for 30 min followed by 60% EtOAc/hexanes for an additional 15 min. The title compound, 2-(2-hydroxybenzyl)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (818 mg, 79% yield) was obtained as yellow solid. MS [M+H]+=463; 1H NMR (CDCl3, 400 MHz) δ 8.54 (s, 1H), 8.14 (s, 1H), 7.32-7.17 (m, 8H), 7.04-7.00 (m, 2H), 6.94 (dd, 1H), 6.81 (td, 1H), 5.13 (s, 2H).

후처리

  1. stirringThe reaction was stirred for an additional 10 min
  2. concentrationthe resultant solution was concentrated under reduced pressure
  3. customThe crude residue was purified
  4. washeluting with a gradient of 0% to 60% EtOAc/hexanes for 30 min
  5. waitfollowed by 60% EtOAc/hexanes for an additional 15 min

출처 및 근거

ORD 기록
ord-d9139a734ea944ada14ef0b19cb37de8
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378418B2

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