Acetic Anhydride → HCID 11603507、化合物

HRID 1432429ノート

反応式

HRID 1432429 の反応式
[C:1](OC(=O)C)(=[O:3])[CH3:2].[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]3[N:21]=[C:20]([CH:22]4[CH2:27][CH2:26][N:25](S(CC5C=CC=CC=5)(=O)=O)[CH2:24][CH2:23]4)[NH:19][C:18]=3[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:16][C:11]=2[O:10][CH2:9]1.C(N(C(C)C)CC)(C)C>C1COCC1>[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]3[N:21]=[C:20]([CH:22]4[CH2:27][CH2:26][N:25]([C:1](=[O:3])[CH3:2])[CH2:24][CH2:23]4)[NH:19][C:18]=3[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:16][C:11]=2[O:10][CH2:9]1

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 10345947HCID 10345947、化合物

生成物 1

HCID 11603507HCID 11603507、化合物収率 26%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Acetic anhydride (0.011 mL, 0.12 mmol) was added to a solution of 2-(5-benzo[1,3]dioxol-5-yl-2-piperidin-4-yl-3H-imidazol-4-yl)-pyridine (0.035 g, 0.10 mmol; prepared as described in Example 11) and diisopropylethylamine (0.021 mL, 0.12 mmol) in anhydrous THF (3 mL). The mixture was stirred at room temperature for 18 hours and was partitioned between ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated. HPLC purification eluting with acetonitrile:water gave 0.010 g (26%) of the title compound as a yellow solid. MS (ESP+) m/z 391.2 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 8.59 (m, 1H), 7.73 (m, 1H), 7.34 (m, 2H), 6.94 (m, 3H), 5.98 (s, 2H), 4.83 (s, 3H), 4.60 (m, 2H), 4.01 (m, 2H), 3.28 (m, 3H), 2.69 (m, 2H).

後処理

  1. customwas partitioned between ethyl acetate and water
  2. washThe organic solution was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customHPLC purification
  7. washeluting with acetonitrile

出典と根拠

ORDレコード
ord-7905c16672ec49c7ad4c389bf779df4e
出典データセット
uspto-grants-2009_11
特許番号
US07612094B2

反応ノート

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