Iodine → 2-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}-1,3,4-oxadiazole

HRID 273068ノート

反応式

HRID 273068 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C.[CH:29]([NH:31][NH:32][C:33]([C:35]1([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][CH2:50][N:51]3[CH2:55][CH2:54][CH2:53][CH2:52]3)=[CH:43][CH:42]=2)[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)=[O:34])=O>ClCCl>[N:51]1([CH2:50][CH2:49][CH2:48][O:47][C:44]2[CH:43]=[CH:42][C:41]([C:35]3([C:33]4[O:34][CH:29]=[N:31][N:32]=4)[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[CH:46][CH:45]=2)[CH2:55][CH2:54][CH2:53][CH2:52]1

参加物

6

反応物 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 68576159N'-formyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbohydrazide

生成物 1

HCID 598374412-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}-1,3,4-oxadiazole収率 20.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

Triphenylphosphine (0.203 g, 0.78 mmol), iodine (0.198 g, 0.78 mmol) and triethylamine (0.217 mL, 1.56 mmol) were dissolved in dichloromethane (5 mL). The mixture was stirred at room temperature for 10 minutes. N′-formyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbohydrazide (0.145 g, 0.39 mmol) in dichloromethane (5 mL) was added. The mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane (100 mL) and washed with water (25 mL). The organic was dried over sodium sulphate, filtered and concentrated in vacuo to provide a yellow oil. This was purified using preparative HPLC on Fraction-Lynx® eluting with water:acetonitrile:trifluoroacetic acid (95:5:0.1) to provide the title compound (0.028 g, 20%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ1.78-1.85 (m, 4H), 2.05 (m, 2H), 2.30 (m, 2H), 2.56-2.60 (m, 4H), 2.60-2.70 (m, 4H), 3.59 (m, 2H), 3.90-4.05 (m, 4H), 6.90 (d, 2H), 7.20 (d, 2H), 8.30 (s, 1H). HRMS ESI+ m/z 358.2117 [MH]+.

後処理

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. washwashed with water (25 mL)
  3. dry with materialThe organic was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a yellow oil
  7. customThis was purified
  8. washeluting with water:acetonitrile:trifluoroacetic acid (95:5:0.1)

出典と根拠

ORDレコード
ord-4ecd098a205f4265befba7e8f9325c6a
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

反応ノート

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