Sodium Iodide → 2-(4-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperazin-1-yl)-acetamide

HRID 1889939ノート

反応式

HRID 1889939 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([N:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)[CH:22]=4)[N:19]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl[CH2:34][C:35]([NH2:37])=[O:36].[I-].[Na+]>C(#N)C.O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH:20][C:21]4[CH:22]=[C:23]([N:27]5[CH2:32][CH2:31][N:30]([CH2:34][C:35]([NH2:37])=[O:36])[CH2:29][CH2:28]5)[CH:24]=[CH:25][CH:26]=4)[N:19]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

参加物

6

反応物 3

HCID 5238Sodium IodideHCID 6580ChloroacetamideHCID 59612339[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-piperazin-1-yl-phenyl)-amine

生成物 1

HCID 596123702-(4-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperazin-1-yl)-acetamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

A suspension of [8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(3-piperazin-1-yl-phenyl)-amine (100.0 mg, 0.2229 mmol), 2-chloroacetamide (23.0 mg, 0.246 mmol) and sodium iodide (3.0 mg, 0.020 mmol) in acetonitrile (2 mL) was stirred and heated at 70° C. for 6 hours. The suspension was cooled to room temperature, diluted with water (30 mL). The precipitate was filtered and rinsed with water. The recovered yellow solid was triturated with methanol (5 mL), filtered and placed under high vacuum overnight. 2-(4-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperazin-1-yl)-acetamide and was isolated as a yellow solid (0.075 g, 67%). MP=271-275° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.62 (s, 1H), 8.86 (d, J=6.5 Hz, 1H), 8.43 (d, J=7.5 Hz, 2H), 8.06 (d, J=7.6 Hz, 2H), 7.96 (d, J=7.5 Hz, 1H), 7.53 (s, 1H), 7.26-7.06 (m, 5H), 6.50 (d, J=6.5 Hz, 1H), 3.29 (s, 3H), 3.20-3.15 (m, 4H), 2.93 (s, 2H), 2.64-2.58 (m, 4H). MS=506 (MH)+.

後処理

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationThe precipitate was filtered
  3. washrinsed with water
  4. customThe recovered yellow solid was triturated with methanol (5 mL)
  5. filtrationfiltered
  6. customplaced under high vacuum overnight

出典と根拠

ORDレコード
ord-e90b9c16ec12425fb7ce01fe3c2d607b
出典データセット
uspto-grants-2013_08
特許番号
US08501936B2

反応ノート

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