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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
Notes
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Reaction equation

HRID 1850742 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-ccf2b6975b1b4b5593f2c8e4648567af
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957062B2

Reaction notes

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