Chloroacetonitrile → HCID 44612144, compound

HRID 1897708Notes

Reaction equation

HRID 1897708 reaction equation
[Cl:1][C:2]1[C:3]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:11][C:10]=2[F:22])=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:37][C:38]#[N:39].[NH4+].[Cl-]>C(#N)C>[Cl:1][C:2]1[C:3]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)=[N:4][C:5]([NH:8][C:9]2[C:10]([F:22])=[CH:11][C:12]([CH:16]3[CH2:17][CH2:18][N:19]([CH2:37][C:38]#[N:39])[CH2:20][CH2:21]3)=[C:13]([CH3:15])[CH:14]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 446126165-chloro-N2-(2-fluoro-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Product 1

HCID 44612144HCID 44612144, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-chloro-N2-(2-fluoro-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (20 mg, 0.048 mmol) in acetonitrile (0.5 mL) was added Cs2CO3 (31 mg, 0.096 mmol) and chloroacetonitrile (7 mg, 0.096 mmol). The resulting mixture was stirred at room temperature for 14 h before it was treated with saturated aqueous NH4Cl (1 mL) and extracted with EtOAc (3×2 mL). The organic layers were combined, concentrated, and the residue was purified by preparative RP-HPLC to provide 2-(4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-5-fluoro-2-methylphenyl)piperidin-1-yl)acetonitrile; ESMS m/z 455.2 (M+H+).

Workup

  1. extractionextracted with EtOAc (3×2 mL)
  2. concentrationconcentrated
  3. customthe residue was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-2dc4ba40f48244e495ba331f0428c536
Source dataset
uspto-grants-2013_08
Patent number
US08519129B2

Reaction notes

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