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Sodium Cyanide → HCID 86627803, compound

HRID 645522
Notes
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Reaction equation

HRID 645522 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[C:22]([C:23](=[O:32])[NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:21]([Cl:33])[N:20]=[C:19](S(C)(=O)=O)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:38]#[N:39].[Na+]>C(Cl)Cl.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[C:22]([C:23](=[O:32])[NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:21]([Cl:33])[N:20]=[C:19]([C:38]#[N:39])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 86627804HCID 86627804, compound

Product 1

HCID 86627803HCID 86627803, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent
HCID 21908982
Water methylene chloride
Solvent

Procedure

To a solution of the above product, 4-[2-(5-benzylcarbamoyl-6-chloro-2-methanesulfonylpyrimidin-4-yloxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester in CH2Cl2/H2O (20 mL/2 mL) is added NaCN (3.3 mmol) and tetra-n-butylammonium bromide (0.14 mmol) at 0° C. After warmed up to room temperature, the reaction mixture is vigorously stirred for 1.5 h at room temperature. The mixture is diluted with CH2Cl2, washed with aq. NaHCO3. The organic layer is dried over Na2SO4, filtered, and concentrated. The residue is purified by silica gel column chromatography to give 4-[2-(5-benzylcarbamoyl-6-chloro-2-cyano-pyrimidin-4-yloxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester as a white solid. 1H-NMR (CDCl3), δ 1.09-1.19 (2H, m), 1.46 (9H, s), 1.63-1.74 (5H, m), 2.66 (2H, br t), 4.07 (2H, m), 4.51 (2H, t), 4.66 (2H, d), 6.11 (1H, t), 7.31-7.37 (5H, m).

Workup

  1. washwashed with aq. NaHCO3
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2640e573bc1c4fac9c52deef5b70aabc
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07704996B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes