Trifluoroacetic acid → HCID 178480986, compound

HRID 897858Notes

Reaction equation

HRID 897858 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:26]3[CH2:31][CH2:30][C@H:29]([N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)[CH2:28][CH2:27]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)OC(C)(C)C)=[C:13]([Cl:25])[CH:12]=3)[C:3]=12.FC(F)(F)C(O)=O>ClCCl>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:4](=[N:5][CH:6]=[N:7][C:2]=3[NH2:1])[N:8]([C@H:26]3[CH2:31][CH2:30][C@H:29]([N:32]4[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]4)[CH2:28][CH2:27]3)[N:9]=2)=[CH:12][C:13]=1[Cl:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178480990HCID 178480990, compound

Product 1

HCID 178480986HCID 178480986, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans tert-butyl N-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-chlorophenyl)carbamate (1.993 g, 0.00368 mol) was added to a solution of 20% trifluoracetic acid in dichloromethane. The mixture was stirred for 2 hours at ambient temperature. The solvent was removed in vacuo and the residue was dissolved in dichloromethane (50 mL) and washed with a 1.0 M aqueous solution of sodium hydroxide (2×25 mL). The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo to give trans 3-(4-amino-3-chlorophenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1.564 g, 0.00355 mol) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (50 mL)
  3. washwashed with a 1.0 M aqueous solution of sodium hydroxide (2×25 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-853e3246b8794b988412794efcf65576
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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