Trifluoroacetic acid methylene chloride → HCID 178488198, compound

HRID 897564Notes

Reaction equation

HRID 897564 reaction equation
FC(F)(F)C(O)=O.ClCCl.[NH2:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]2[N:18]([CH:33]3[CH2:38][CH2:37][CH:36]([N:39]4[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]4)[CH2:35][CH2:34]3)[N:19]=[C:20]([C:21]3[CH:26]=[CH:25][C:24]([NH:27]C(=O)[O-])=[C:23]([O:31][CH3:32])[CH:22]=3)[C:13]=12>ClCCl>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[C:13]3[C:14](=[N:15][CH:16]=[N:17][C:12]=3[NH2:11])[N:18]([C@H:33]3[CH2:38][CH2:37][C@H:36]([N:39]4[CH2:40][CH2:41][N:42]([CH3:45])[CH2:43][CH2:44]4)[CH2:35][CH2:34]3)[N:19]=2)=[CH:22][C:23]=1[O:31][CH3:32]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 22346847N-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)carbamate

Product 1

HCID 178488198HCID 178488198, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trifluoroacetic acid/dichloromethane (20:80, 150 mL) was added to a solution of N-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)carbamate(4.75 g, 8.85 mmol) in dichloromethane (100 mL) at 0° C. 2 hours later, the ice-bath was removed and the solvents were evaporated and the residue was dissolved in dichloromethane. Sodium hydroxide (1.0N) was added to adjust the pH to about 10. The solid formed upon removal of organic solvent was collect by filtration to give trans-3-(4-amino-3-methoxyphenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (3.85 g, 100%). 1H NMR (DMSO-d6) δ 1.44(m, 2H), 1.96 (m, 6H), 2.21 (s, 3H), 2.33 (m, 5H), 2.53 (m, 4H), 3.83 (s, 3H), 4.60 (m, 1H), 5.03 (bs, 2H), 6.76 (d, J=7.91 Hz, 1H), 6.98 (d, J=7.89 Hz, 1H), 7.03 (m, 2H), 8.19 (s, 1H).

Workup

  1. custom2 hours later, the ice-bath was removed
  2. customthe solvents were evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. additionSodium hydroxide (1.0N) was added
  5. customThe solid formed upon removal of organic solvent
  6. filtrationwas collect by filtration

Sources & evidence

ORD record
ord-01aa5cae04624e60804064ee0512018c
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…