Benzyl isocyanate → HCID 178476645, compound

HRID 432199

Reaction equation

HRID 432199 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[N:9]=2)=[CH:4][C:3]=1[O:31][CH3:32].[CH2:33]([N:40]=[C:41]=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>N1C=CC=CC=1>[C:3]([OH:31])(=[O:42])[CH3:4].[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[CH2:20][CH2:19]3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:41]([NH:40][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:42])=[C:3]([O:31][CH3:32])[CH:4]=3)[C:16]=12

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 178488197HCID 178488197, compound

Product 1

HCID 178476645HCID 178476645, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cis-3-(4-amino-3-methoxyphenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.082 g, 0.000188 mol) was dissolved in anhydrous pyridine (1 mL), benzyl isocyanate (0.025 g, 0.000188 mol) was added and the resulting solution was stirred at ambient temperature for 20 hours. The solvent was removed under reduced pressure and the resulting residue purified by preparative HPLC (Hypersil C 18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield cis-N-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-N′-benzylurea acetate (0.009 g, 0.0000142 mol) as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting residue purified by preparative HPLC (Hypersil C 18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

Sources & evidence

ORD record
ord-a9354a05a00e41c69d8566e72ce47a38
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Linked notes

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