Chloroacetyl chloride → HCID 22347363, compound

HRID 432506Notes

Reaction equation

HRID 432506 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]3=[N:10][CH:11]=[N:12][C:13]([NH2:14])=[C:8]3[C:7]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)=[N:6]2)[CH2:2]1.C(=O)([O-])[O-:29].[K+].[K+].Cl[CH2:35][C:36](Cl)=[O:37].S(O)(O)(=O)=O.[NH2:44][C:45]1[NH:46][CH:47]=[CH:48][N:49]=1>CN(C)C=O>[C:22]([OH:29])(=[O:21])[CH3:27].[NH2:44][C:45]1[N:46]([CH2:35][C:36]([N:1]2[CH2:2][CH:3]([N:5]3[C:9]4=[N:10][CH:11]=[N:12][C:13]([NH2:14])=[C:8]4[C:7]([C:15]4[CH:16]=[CH:17][C:18]([O:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:19][CH:20]=4)=[N:6]3)[CH2:4]2)=[O:37])[CH:47]=[CH:48][N:49]=1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium Carbonate2×HCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 223471371-(3-azetanyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 22347363HCID 22347363, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(3-azetanyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.05 g, 0.00014 mol) and potassium carbonate (0.039 g, 0.00028 mol) in anhydrous N,N-dimethylformamide (3 mL) was added chloroacetylchloride (0.0031 g, 0.00028 mol) at room temperature. The mixture was stirred for 10 min. before 2-aminoimidazole sulfate (0.18 g, 0.0014 mol) and potassium carbonate (0.19 g, 0.0014 mol) was added. The mixture was stirred at room temperature for 2 days then warmed to 60° C. for 6 hours. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (3 mL) and washed with water (2 mL). The solvent was removed under reduced pressure. The residue was purified by RP-HPLC (Hypersilprep HS C18, 8 μm, 250×21.1 mm; 5%-100% over 35 min with 0.1 M ammonium acetate, 21 mL/min) to yield 2-(2-amino-1H-1-imidazolyl)-1-{3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-azetanyl}-1-ethanone acetate (0.006 g, 0.00001 mol).

Workup

  1. additionwas added
  2. temperaturethen warmed to 60° C. for 6 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (3 mL)
  5. washwashed with water (2 mL)
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by RP-HPLC (Hypersilprep HS C18, 8 μm, 250×21.1 mm; 5%-100% over 35 min with 0.1 M ammonium acetate, 21 mL/min)

Sources & evidence

ORD record
ord-36f7e9242387480d9bcc86c9014b4f68
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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