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

HRID 17535노트

반응식

HRID 17535 반응식
[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]

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 120273N-IodosuccinimideHCID 68587091HCID 68587091, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4cf1b0752dda4e728e91284f340d5807
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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