Ethanol → 6-Iodo-3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-[1,2,4]triazolo[4,3-a]pyridine

HRID 1041901ノート

反応式

HRID 1041901 の反応式
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8]/[N:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:12]=2)=[N:6][CH:7]=1.CCO>C(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[CH:12]=3)=[N:9][N:8]=2)[CH:7]=1

参加物

4

反応物 2

HCID 702EthanolHCID 872226535-iodo-N-[(E)-[3-(2-morpholin-4-ylethoxy)phenyl]methylideneamino]pyridin-2-amine

生成物 1

HCID 669775456-Iodo-3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-[1,2,4]triazolo[4,3-a]pyridine収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of Example 1 step a (10.93 g, 24.16 mmol) in DCM (100 mL)/EtOH (15 mL), was added Phl(OAc)2 (10.74 g, 33.35 mmol). The reaction was stirred at RT for 72 h, diluted with DCM (25 mL) then washed with aq. sodium hydroxide (1 M, 25 mL) and brine (25 mL). The organic layer was dried (MgSO4), filtered, and the filtrate was concentrated in vacuo. The residue was triturated with Et2O (10 mL) and the resulting solid was collected by filtration to afford the title compound (9.98 g, 92%) as an off-white solid. LCMS (Method 1): Rt 2.11 min, m/z 451 [MH+]. 1H NMR (400 MHz, DMSO-d6): δ 8.69 (1 H, s), 7.71 (1 H, d, J 9.5), 7.60 (1 H, d, J 9.5), 7.53 (1 H, t, J 7.9), 7.47-7.41 (2 H, m), 7.18 (1 H, d, J 8.1), 4.21 (2 H, t, J 5.7), 3.59 (4 H, t, J 4.5), 2.75 (2 H, t, J 5.7), 2.45 (4 H, m).

後処理

  1. washthen washed with aq. sodium hydroxide (1 M, 25 mL) and brine (25 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was triturated with Et2O (10 mL)
  6. filtrationthe resulting solid was collected by filtration

出典と根拠

ORDレコード
ord-16b67d99f3e24b36bf0a39d0915bf042
出典データセット
uspto-grants-2013_10
特許番号
US08557797B2

反応ノート

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