Chloroform → 4-Amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-iodobiphenyl-3-carbonitrile

HRID 17535ノート

反応式

HRID 17535 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][C@H:10]([N:13]([CH3:15])[CH3:14])[CH2:9]2)[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][C:3]=1[C:22]#[N:23].[I:24]N1C(=O)CCC1=O.C(Cl)(Cl)Cl.[OH-].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[C:7]([I:24])=[C:6]([N:8]2[CH2:12][CH2:11][C@H:10]([N:13]([CH3:14])[CH3:15])[CH2:9]2)[C:5]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:4][C:3]=1[C:22]#[N:23]

参加物

6

反応物 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 120273N-IodosuccinimideHCID 68587091HCID 68587091、化合物

生成物 1

HCID 866308704-Amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-iodobiphenyl-3-carbonitrile収率 63%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

4-Amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]biphenyl-3-carbonitrile (I-243) (75 mg, 0.25 mmol) was dissolved in acetic acid (1 ml), and at room temperature, N-iodosuccinimide (66 mg, 0.29 mmol) was added. After stirring under nitrogen atmosphere at the same temperature for 6 hours, the reaction liquid was fractionated with chloroform and aqueous 1 M sodium hydroxide solution. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1) to obtain the entitled compound (67 mg, 63%) as a brown gel.

後処理

  1. customthe reaction liquid
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insoluble matter was separated by filtration
  5. customthe solvent was evaporated away
  6. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1)

出典と根拠

ORDレコード
ord-4cf1b0752dda4e728e91284f340d5807
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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