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Cyanogen Bromide → 4-[(1R,2S)-2-(2-{[3-methyl-5-(2-oxoimidazolidin-1-yl)pyridine-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carbonitrile

HRID 1850742
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HRID 1850742 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([N:20]2[CH2:24][CH2:23][NH:22][C:21]2=[O:25])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH2:10][C@@H:11]1[CH2:13][C@@H:12]1[CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+].[N:32]#[C:33]Br>C(Cl)Cl>[CH3:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][C@@H:11]2[CH2:13][C@@H:12]2[CH:14]2[CH2:19][CH2:18][N:17]([C:33]#[N:32])[CH2:16][CH2:15]2)=[N:6][CH:5]=[C:4]([N:20]2[CH2:24][CH2:23][NH:22][C:21]2=[O:25])[CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 867111881-(5-methyl-6-{2-[(1S,2R)-2-piperidin-4-ylcyclopropyl]ethoxy}pyridine-3-yl)imidazolidin-2-one

생성물 1

HCID 867111894-[(1R,2S)-2-(2-{[3-methyl-5-(2-oxoimidazolidin-1-yl)pyridine-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
3회

실험 절차

To a solution of 1-(5-methyl-6-{2-[(1S,2R)-2-piperidine-4-ylcyclopropyl]ethoxy}pyridine-3-yl)imidazolidin-2-one (12 mg, 0.035 mmol) in 1.5 mL of DCM was added K2CO3 (14.5 mg, 0.105 mmol, in 0.5 mL of water) at room temperature followed by addition of cyanogen bromide (0.014 mL of 3M soln in DCM, 0.042 mmol) via syringe at room temperature. The mixture was then stirred for 30 min at room temperature and then diluted with 2 mL DCM. The solution was washed with sat'd NaHCO3 aq. soln, separated, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. The crude product was used without further purification. LCMS (ESI) m/z 370 [M+H]+.

후처리

  1. washThe solution was washed with sat'd NaHCO3 aq. soln
  2. customseparated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe crude product was used without further purification

출처 및 근거

ORD 기록
ord-ccf2b6975b1b4b5593f2c8e4648567af
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957062B2

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