Ethanolamine → HCID 22347389, compound

HRID 432510Notes

Reaction equation

HRID 432510 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-].[K+].[K+].Cl[CH2:37][C:38](Cl)=[O:39].[CH2:41]([CH2:43][NH2:44])[OH:42]>CN(C)C=O>[NH2:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:16]([CH:24]3[CH2:29][CH2:28][N:27]([C:38](=[O:39])[CH2:37][NH:44][CH2:43][CH2:41][OH:42])[CH2:26][CH2:25]3)[N:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][CH:12]=3)[C:22]=12

Participants

6

Reactant 4

HCID 700EthanolamineHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 223472623-(4-phenoxyphenyl)-1-(piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 22347389HCID 22347389, compoundYield 38.5%

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 ethanolamine (0.078 mL, 0.0013 mol) was added. The mixture was stirred at room temperature for 18 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 1-{4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidino}-2-[(2-hydroxyethyl)amino]-1-ethanone (0.022 g, 0.00005 mol).

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (3 mL)
  4. washwashed with water (2 mL)
  5. customThe solvent was removed under reduced pressure
  6. 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-566b209ea3384ccfac7d185d5deb5625
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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