Water → HCID 24966199、化合物

HRID 1666519ノート

反応式

HRID 1666519 の反応式
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[C:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:17]=2)=[N:13][CH:14]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:36](=O)[O:37]C2C=CC=CC=2)[N:30]=1.C(N(CC)CC)C.O>CS(C)=O>[F:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=2)[CH:22]=[C:23]2[CH2:24][CH2:25][N:26]([C:36]([NH:35][C:31]3[N:30]=[N:29][CH:34]=[CH:33][CH:32]=3)=[O:37])[CH2:27][CH2:28]2)=[N:13][CH:14]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 20150036Phenyl pyridazin-3-ylcarbamateHCID 66876197HCID 66876197、化合物

生成物 1

HCID 24966199HCID 24966199、化合物収率 42%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of 5-fluoro-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetate (0.466 g), phenyl pyridazin-3-ylcarbamate (0.274 g, 1.40 equiv), and triethylamine (0.634 mL, 5.00 equiv) in dimethyl sulfoxide (2.0 mL, 0.30 M) was heated to 65° C. for 2 h. The reaction was cooled to room temperature. Water was added and then the solution was extracted with ethyl acetate (3 times). The organic extracts were combined and washed with water, dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a 12 g silica gel column using 20-50% ethyl acetate/dichloromethane over 60 minutes as the eluent to give the title compound as a yellow foam. 0.155 g, 42% yield. 1H NMR (400 MHz, CDCl3) δ ppm 2.46 (2H, t, J=5.5 Hz), 2.59 (2H, t, J=5.5 Hz), 3.61 (2H, t, J=5.8 Hz), 3.71 (2H, t, J=5.8 Hz), 6.39 (1H, s), 6.84-6.99 (3H, m), 7.02 (1H, d, J=7.8 Hz), 7.34 (1H, t, J=7.8 Hz), 7.39-7.54 (2H, m), 8.02 (1H, d, J=3.1 Hz), 8.47 (1H, d, J=8.6 Hz), 8.74 (1H, d, J=3.5 Hz).

後処理

  1. extractionthe solution was extracted with ethyl acetate (3 times)
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on a 12 g silica gel column
  7. customover 60 minutes

出典と根拠

ORDレコード
ord-2593945ce2dd4ade9f6e24981cac461b
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

反応ノート

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