Methanol → Methyl (6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazin-3-yl)carbamate

HRID 1714869노트

반응식

HRID 1714869 반응식
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[N:16][C:15](C(O)=O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.CCN(CC)CC.[CH3:51][OH:52].C[N:54]([CH:56]=[O:57])C>O>[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[N:17]=[N:16][C:15]([NH:54][C:56](=[O:57])[O:52][CH3:51])=[CH:14][CH:13]=2)[CH2:10][CH2:11]1

참가 물질

7

반응물 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 462254266-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxylic acid

생성물 1

HCID 23630218Methyl (6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazin-3-yl)carbamate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxylic acid (150 mg, 0.4 mmol), DPPA (100 μL, 0.46 mmol) and Et3N (65 μL, 0.46 mmol) in DMF (1.5 mL) was stirred at r.t. overnight. MeOH (150 μL, 3.7 mmol) was then added and the mixture was heated at 65-70° C. for 6 h. After cooling, the mixture was diluted with water and extracted with EtOAc. The EtOAc extract was washed twice with water, dried (Na2SO4) and concentrated. CombiFlash chromatography (10 g, 40-80% EtOAc in hexanes in 20 min, 20 mL/min, 15 mL/fraction) gave the title compound as a white solid. 1H NMR (500 MHz, acetone-d6): δ 1.89-1.97 (m, 2H), 2.15 (m, 2H), 3.65-3.71 (m, 2H), 3.76 (s, 3H), 3.87-3.93 (m, 2H), 4.94-4.98 (m, 1H), 7.11 (t, 1H), 7.37 (m, 2H), 7.61-7.67 (m, 2H), 8.00 (d, 1H), 9.11 (s, 1H). MS (+ESI) m/z 397 (MH+).

후처리

  1. temperaturethe mixture was heated at 65-70° C. for 6 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed twice with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3eec4911fb6d40568dbefcf2df079463
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799787B2

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