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

HRID 1714869ノート

反応式

HRID 1714869 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-3eec4911fb6d40568dbefcf2df079463
出典データセット
uspto-grants-2010_09
特許番号
US07799787B2

反応ノート

読み込み中…