2-Chlorobenzyl chloroformate → HCID 11584392、化合物

HRID 1432428ノート

反応式

HRID 1432428 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:3].[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]3[N:26]=[C:25]([CH:27]4[CH2:32][CH2:31][N:30](S(CC5C=CC=CC=5)(=O)=O)[CH2:29][CH2:28]4)[NH:24][C:23]=3[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=3)=[CH:21][C:16]=2[O:15][CH2:14]1>C1COCC1.C(=O)(O)[O-].[Na+]>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][O:4][C:2]([N:30]1[CH2:29][CH2:28][CH:27]([C:25]2[NH:24][C:23]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=3)=[C:22]([C:20]3[CH:19]=[CH:18][C:17]4[O:13][CH2:14][O:15][C:16]=4[CH:21]=3)[N:26]=2)[CH2:32][CH2:31]1)=[O:3]

参加物

5

反応物 2

HCID 40723422-Chlorobenzyl chloroformateHCID 10345947HCID 10345947、化合物

生成物 1

HCID 11584392HCID 11584392、化合物収率 85.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

2-Chlorobenzyl chloroformate (0.011 mL, 0.070 mmol) was added to a solution of 2-(5-benzo[1,3]dioxol-5-yl-2-piperidin-4-yl-3H-imidazol-4-yl)-pyridine (0.021 g, 0.059 mmol; prepared as described in Example 11) in a mixture of THF (3 mL) and 2 M sodium bicarbonate aqueous solution (0.3 mL). The mixture was stirred at room temperature for 2 hours. Mixture 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 0.026 g (70%) of the title compound as a yellow solid. MS (ESP+) m/z 517.03 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.60 (m, 1H), 7.81 (m, 1H), 7.60 (d, 1H, J=8.2 Hz), 7.39 (m, 3H), 7.27 (m, 2H), 7.07 (dd, 1H, J=8.1, 1.8 Hz), 6.99 (d, 1H, J=1.8 Hz), 6.90 (d, 1H, J=8.1 Hz), 6.05 (s, 2H), 5.24 (s, 2H), 4.36 (m, 2H), 3.48 (m, 1H), 2.98 (m, 2H), 2.17 (m, 2H), 1.86 (m, 2H).

後処理

  1. customMixture was 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-c4025974f2e744aaa92e95372d3a30cf
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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