Chloroacetyl chloride → HCID 22347043, compound

HRID 432509Notes

Reaction equation

HRID 432509 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[N:16]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:31].[K+].[K+].Cl[CH2:37][C:38](Cl)=[O:39].S(O)(O)(=O)=O.[NH2:46][C:47]1[NH:48][CH:49]=[CH:50][N:51]=1>CN(C)C=O>[C:8]([OH:31])(=[O:1])[CH3:13].[NH2:46][C:47]1[N:48]([CH2:37][C:38]([N:27]2[CH2:28][CH2:29][CH:24]([N:16]3[C:17]4=[N:18][CH:19]=[N:20][C:21]([NH2:23])=[C:22]4[C:14]([C:11]4[CH:10]=[CH:9][C:8]([O:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[CH:13][CH:12]=4)=[N:15]3)[CH2:25][CH2:26]2)=[O:39])[CH:49]=[CH:50][N:51]=1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium Carbonate2×HCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 223472623-(4-phenoxyphenyl)-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 22347043HCID 22347043, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(4-phenoxyphenyl)-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.05 g, 0.00013 mol) and potassium carbonate (0.036 g, 0.00026 mol) in anhydrous N,N-dimethylformamide (3 mL) was added chloroacetylchloride (0.028 g, 0.00026 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) were added. The mixture was stirred at room temperature for 18 hours 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-{4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidino}-1-ethanone acetate (0.015 g, 0.00003 mol).

Workup

  1. additionwere 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-896186e7a71c4cc0916a66b22dd1a193
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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