Dimethylformamide → (1S,2S)-2-(4-(5-((5-Chloropyridin-2-yl)thio)-1-methyl-1H-imidazol-4-yl)phenyl)-N,N-dimethylcyc

HRID 1183209ノート

反応式

HRID 1183209 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[CH:12]=[N:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([C@H:21]3[CH2:23][C@@H:22]3[C:24]([NH:26][CH3:27])=[O:25])=[CH:17][CH:16]=2)=[N:6][CH:7]=1.[H-].[Na+].[CH3:30]N(C=O)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[CH:12]=[N:11][C:10]=2[C:15]2[CH:20]=[CH:19][C:18]([C@H:21]3[CH2:23][C@@H:22]3[C:24]([N:26]([CH3:30])[CH3:27])=[O:25])=[CH:17][CH:16]=2)=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 46908962HCID 46908962、化合物

生成物 1

HCID 46909057(1S,2S)-2-(4-(5-((5-Chloropyridin-2-yl)thio)-1-methyl-1H-imidazol-4-yl)phenyl)-N,N-dimethylcyc

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

[11C]MeI (from Step 1) was trapped in a RT mixture of (1S,2S)-2-(4-{5-[(5-chloropyridin-2-yl)thio]-1-methyl-1H-imidazol-4-yl}phenyl)-N-methylcyclopropane-carboxamide (product of Example 6, 0.25 mg) in DMF (0.25 mL) containing 16 ul of NaH (0.5 g/20 mL DMF). The reaction mixture was transferred to a 2 mL v-vial at 65° C., heated for 5 minutes, diluted with H2O (0.8 mL) and injected onto the HPLC (Gemini C18, 10×150 mm, Phenomenex). The desired peak was eluted with a solvent system containing 25% A and 75% B (A=MeCN, B=95:5:0.1H2O:MeCN:TFA, 5 ml/min, retention time ˜6.5 minutes) and collected in a heated round bottom flask on a rotary evaporator. The solution was concentrated and vacuum transferred to a septum capped 5 mL v-vial. The round bottom flask was rinsed with ethanol (0.1 mL) and saline (1-2 mL) and vacuum transferred to the same v-vial to give 13.6 mCi of [11C] (1S,2S)-2-(4-{5-[(5-chloropyridin-2-yl)thio]-1-methyl-1H-imidazol-4-yl}phenyl)-N,N-dimethyl-cyclopropanecarboxamide.

後処理

  1. customwas trapped in a RT
  2. customwas transferred to a 2 mL v-vial at 65° C.
  3. temperatureheated for 5 minutes
  4. washThe desired peak was eluted with a solvent system
  5. additioncontaining 25% A and 75% B (A=MeCN, B=95:5:0.1H2O
  6. customMeCN:TFA, 5 ml/min, retention time ˜6.5 minutes) and collected in a heated round bottom flask on a rotary evaporator
  7. concentrationThe solution was concentrated
  8. customcapped 5 mL v-vial
  9. washThe round bottom flask was rinsed with ethanol (0.1 mL) and saline (1-2 mL) and vacuum

出典と根拠

ORDレコード
ord-628435089f6f4c92b8861ec89f3224b9
出典データセット
uspto-grants-2014_03
特許番号
US08664253B2

反応ノート

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