Trifluoroacetic acid → 5-[2-Amino-5-({4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}ethynyl)pyrimidin-4-yl]-2-(5-chloro-2-methylphenyl)-1H-pyrrole-3-carboxamide

HRID 1403225Notes

Reaction equation

HRID 1403225 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[N:14]=[C:13]([C:15]2[N:19](COCC[Si](C)(C)C)[C:18]([C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=3[CH3:35])=[C:17]([C:36]([NH2:38])=[O:37])[CH:16]=2)[C:12]([C:39]#[C:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([N:49]3[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]3)=[O:48])=[CH:43][CH:42]=2)=[CH:11][N:10]=1>C(Cl)Cl>[NH2:8][C:9]1[N:14]=[C:13]([C:15]2[NH:19][C:18]([C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=3[CH3:35])=[C:17]([C:36]([NH2:38])=[O:37])[CH:16]=2)[C:12]([C:39]#[C:40][C:41]2[CH:42]=[CH:43][C:44]([C:47]([N:49]3[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]3)=[O:48])=[CH:45][CH:46]=2)=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867252955-[2-Amino-5-({4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}ethynyl)pyrimidin-4-yl]-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide

Product 1

HCID 712395935-[2-Amino-5-({4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}ethynyl)pyrimidin-4-yl]-2-(5-chloro-2-methylphenyl)-1H-pyrrole-3-carboxamideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.4 mL) was added to a solution of 5-[2-amino-5-({4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}ethynyl)pyrimidin-4-yl]-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (0.110 g, 0.14 mmol) in dry DCM (2.8 mL) and stirred for 4 h at room temperature. After solvent removal, the residue was treated with EtOH (3 mL), 33% NH4OH (0.4 mL) and stirred for 0.5 h. The solvent was evaporated to dryness and the residue was purified by flash-chromatography on silica gel (DCM/MeOH/7N NH3 in MeOH 94/5/1) to afford the title compound as white solid (0.055 g, 71%).

Workup

  1. customAfter solvent removal
  2. additionthe residue was treated with EtOH (3 mL), 33% NH4OH (0.4 mL)
  3. stirringstirred for 0.5 h
  4. customThe solvent was evaporated to dryness
  5. customthe residue was purified by flash-chromatography on silica gel (DCM/MeOH/7N NH3 in MeOH 94/5/1)

Sources & evidence

ORD record
ord-e62b8d79f6384d1a94472afc6d8cf57d
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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