Chloroacetyl chloride → 2-chloro-N-(4-(2-(4-morpholinophenylamino)pyrimidin-4-yl)phenyl)acetamide

HRID 2091960Notes

Reaction equation

HRID 2091960 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:9]=2)=[CH:4][CH:3]=1.[Cl:27][CH2:28][C:29](Cl)=[O:30]>C1COCC1>[Cl:27][CH2:28][C:29]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[CH:19][CH:20]=3)[N:9]=2)=[CH:4][CH:3]=1)=[O:30]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 248780154-(4-aminophenyl)-N-(4-morpholinophenyl)pyrimidin-2-amine

Product 1

HCID 579909132-chloro-N-(4-(2-(4-morpholinophenylamino)pyrimidin-4-yl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask charged with 4-(4-aminophenyl)-N-(4-morpholinophenyl)pyrimidin-2-amine (100 mg, 0.286 mmol) and THF (1 mL) was added chloroacetyl chloride (0.0230 mL, 0.286 mmol). The solution was stirred at ambient temperature for 1 hour. The crude mixture was then concentrated and used without further purification. LCMS: m/z 424 (M+H)+.

Workup

  1. concentrationThe crude mixture was then concentrated
  2. customused without further purification

Sources & evidence

ORD record
ord-882c2872663f483abf9c2e654ae8217f
Source dataset
uspto-grants-2013_05
Patent number
US08440663B2

Reaction notes

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