Ammonium Chloride → 6-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxamide

HRID 1714865ノート

反応式

HRID 1714865 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:18]([OH:20])=O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.C1C=CC2N(O)N=[N:33]C=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+].C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[F:1][C:2]([F:25])([F:26])[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]([C:18]([NH2:33])=[O:20])=[CH:14][CH:13]=2)[CH2:10][CH2:11]1

参加物

8

反応物 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 462254266-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxylic acid

生成物 1

HCID 462254256-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxylic acid (250 mg, 0.7 mmol), HOBt (92 mg, 0.7 mmol), HATU (518 mg, 1.4 mmol) and ammonium chloride (74 mg, 1.4 mmol) in DMF (5 mL) was added N,N-diisopropylethylamine (592 μL, 3.4 mmol) at room temperature. The mixture was stirred at room temperature overnight, diluted with water and extracted with EtOAc. The organic extract was washed twice with 1N NaOH, brine, dried (Na2SO4) and concentrated. CombiFlash chromatography (10 g, 80-100% EtOAc in hexanes, 20 mL/min, 18 mL/fraction) gave the title compound as a white powder. 1H NMR (400 MHz, acetone-d6): δ 1.93-1.99 (m, 2H), 2.14-2.20 (m, 2H), 3.93-4.09 (m, 4H), 5.05 (s, 1H), 6.72 (s, 1H), 7.13 (t, 1H), 7.38 (m, 2H), 7.62-7.68 (m, 2H), 7.84 (s, 1H), 7.94 (d, 1H). MS (+ESI) m/z 367 (MH+).

後処理

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed twice with 1N NaOH, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-70f9858284274712a18b1aba533877ed
出典データセット
uspto-grants-2010_09
特許番号
US07799787B2

反応ノート

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