Iodoethane → HCID 44611102, compound

HRID 536378Notes

Reaction equation

HRID 536378 reaction equation
[NH2:1][C:2]([CH3:35])([CH3:34])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([NH:18][C:19]3[N:24]=[C:23]([NH:25][C:26]4[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=4)[C:22]([Cl:32])=[CH:21][N:20]=3)=[CH:13][C:12]=2[CH3:33])[CH2:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:42](I)[CH3:43].[NH4+].[Cl-]>CC(C)=O>[Cl:32][C:22]1[C:23]([NH:25][C:26]2[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=2)=[N:24][C:19]([NH:18][C:14]2[C:15]([CH3:17])=[CH:16][C:11]([CH:8]3[CH2:7][CH2:6][N:5]([C:3](=[O:4])[C:2]([NH:1][CH2:42][CH3:43])([CH3:35])[CH3:34])[CH2:10][CH2:9]3)=[C:12]([CH3:33])[CH:13]=2)=[N:20][CH:21]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 58254945HCID 58254945, compound

Product 1

HCID 44611102HCID 44611102, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-amino-1-(4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)piperidin-1-yl)-2-methylpropan-1-one (6 mg, 0.012 mmol) in acetone (0.5 mL) was added K2CO3 (11 mg, 0.079 mmol). The mixture was stirred at room temperature for 10 min. before the addition of EtI (6 mg, 0.038 mmol). The resulting mixture was then 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 thin layer chromatography (silica gel, 8% MeOH/DCM/NH3) followed by further purification with preparative RP-HPLC to provide 1-(4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)piperidin-1-yl)-2-(ethylamino)-2-methylpropan-1-one; ESMS m/z 525.3 (M+H+).

Workup

  1. extractionextracted with EtOAc (3×2 mL)
  2. concentrationconcentrated
  3. customthe residue was purified by preparative thin layer chromatography (silica gel, 8% MeOH/DCM/NH3)
  4. customfollowed by further purification with preparative RP-HPLC

Sources & evidence

ORD record
ord-e142a572e8b3438d9eb4dd57acd75e6d
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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