Trichloroisocyanuric Acid → {5-Chloro-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-cyclopropylamine

HRID 2233116ノート

反応式

HRID 2233116 の反応式
[Cl:1]N1C(=O)N(Cl)C(=O)N(Cl)C1=O.[CH:13]1([NH:16][C:17]2[N:22]=[C:21]([C:23]3[N:27]4[CH:28]=[CH:29][N:30]=[C:31]([CH3:32])[C:26]4=[N:25][C:24]=3[C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[CH:20]=[CH:19][N:18]=2)[CH2:15][CH2:14]1>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:20]1[C:21]([C:23]2[N:27]3[CH:28]=[CH:29][N:30]=[C:31]([CH3:32])[C:26]3=[N:25][C:24]=2[C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)=[N:22][C:17]([NH:16][CH:13]2[CH2:15][CH2:14]2)=[N:18][CH:19]=1

参加物

5

反応物 2

HCID 6909Trichloroisocyanuric AcidHCID 58869555Cyclopropyl-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamine

生成物 1

HCID 58869564{5-Chloro-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-cyclopropylamine収率 95%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

Trichloroisocyanuric acid (0.001 g, 0.04 mmol) was added portion-wise to a refluxing mixture of cyclopropyl-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamine (Example #A.2.1, 0.050 g, 0.14 mmol) in CHCl3 (2.5 mL). The reaction mixture was refluxed for 3 h, cooled to room temperature, diluted with DCM and washed with a saturated aqueous solution of Na2CO3. The organic phase was dried over MgSO4, filtered, and evaporated. The resulting residue was purified by silica gel chromatography using a gradient of heptane/EtOAc (50:50 to 0:100) to afford 0.015 g (27%) of the title compound. LC/MS (Table 1, Method g) Rt=2.71 min; MS m/z: 393.2 (M+H)+.

後処理

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. washwashed with a saturated aqueous solution of Na2CO3
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-ac8d23d1cb1a4aea810109c80e9d4a81
出典データセット
uspto-grants-2010_05
特許番号
US07709468B2

反応ノート

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