Trifluoroacetic acid → Tacedinaline

HRID 1776956Notes

Reaction equation

HRID 1776956 reaction equation
[C:1]([NH:4][C:5]1[CH:27]=[CH:26][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18]C(=O)OC(C)(C)C)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:4][C:5]1[CH:27]=[CH:26][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58433956HCID 58433956, compound

Product 1

HCID 2746Tacedinaline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a 0° C. solution of tert-butyl (2-(4-acetamidobenzamido)phenyl) carbamate 1.5 (3.5 g, 9.5 mmol) in dry dichloromethane (55 mL) was added trifluoroacetic acid (22 mL) dropwise. The mixture was allowed to slowly warm to 23° C. for 2 hours until the reaction was complete. The solvents were removed in vacuo. The reaction mixture was diluted with water and the pH was adjusted to ˜8 with a saturated aqueous solution of sodium bicarbonate. The resulting precipitate was filtered, washed with water and ether, and dried under vacuum to afford 4-acetamido-N-(2-aminophenyl)benzamide 1.6 as an off-white solid. Yield 1.6=2.4 g (96%).

Workup

  1. customThe solvents were removed in vacuo
  2. additionThe reaction mixture was diluted with water
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water and ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f96dd0de1c1a45449e0265df0c1255f6
Source dataset
uspto-grants-2016_02
Patent number
US09266822B2

Reaction notes

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