Trifluoroacetic acid → HCID 24753858, compound

HRID 1919920Notes

Reaction equation

HRID 1919920 reaction equation
FC(F)(F)C(O)=O.[NH:8]([C:15](=[O:49])[CH:16]([C:21]1[CH:48]=[CH:47][C:24]([C:25]([NH:27][C:28]2[CH:33]=[C:32]([C:34]3[CH:38]=[CH:37][S:36][CH:35]=3)[CH:31]=[CH:30][C:29]=2[NH:39]C(=O)OC(C)(C)C)=[O:26])=[CH:23][CH:22]=1)[CH2:17][N:18]([CH3:20])[CH3:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:39][C:29]1[CH:30]=[CH:31][C:32]([C:34]2[CH:38]=[CH:37][S:36][CH:35]=2)=[CH:33][C:28]=1[NH:27][C:25](=[O:26])[C:24]1[CH:47]=[CH:48][C:21]([CH:16]([CH2:17][N:18]([CH3:20])[CH3:19])[C:15]([NH:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:49])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 69483281HCID 69483281, compound

Product 1

HCID 24753858HCID 24753858, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the trifluoroacetic acid salt of tert-butyl [2-[(4-{2-anilino-1-[(dimethylamino)methyl]-2-oxoethyl}benzoyl)amino]-4-(3-thienyl)phenyl]carbamate (374 mg, 0.54 mmol) in CH2Cl2 (8 mL) was added trifluoroacetic acid (2 mL), and the reaction was stirred at room temperature for 1 h. Concentration yielded a yellow residue that was purified by reverse phase HPLC (10-70% MeCN/water). The resulting solid was dissolved in CH2Cl2 (with a small amount of MeOH), neutralized with sat. NaHCO3, washed with brine, dried (MgSO4), and evaporated to yield N-[2-amino-5-(3-thienyl)phenyl]-4-{2-anilino-1-[(dimethylamino)methyl]-2-oxoethyl}benzamide as an off-white solid.

Workup

  1. concentrationConcentration
  2. customyielded a yellow residue that
  3. customwas purified by reverse phase HPLC (10-70% MeCN/water)
  4. dissolutionThe resulting solid was dissolved in CH2Cl2 (with a small amount of MeOH),
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-554389df808d4f5e863b8a824a826c53
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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