Trifluoroacetic acid → HCID 44456312, compound

HRID 1454227Notes

Reaction equation

HRID 1454227 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([CH:24]([CH3:26])[CH3:25])[CH2:20][CH2:19]2)=[O:17])[CH:13]=[CH:12][C:11]=1[O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=1)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:35][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[Cl:34])[O:27][C:11]1[CH:12]=[CH:13][C:14]([C:16]([N:18]2[CH2:19][CH2:20][N:21]([CH:24]([CH3:25])[CH3:26])[CH2:22][CH2:23]2)=[O:17])=[CH:15][C:10]=1[CH2:9][NH:7][CH3:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68848219HCID 68848219, compound

Product 1

HCID 44456312HCID 44456312, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(3,4-dichloro-phenoxy)-5-(4-isopropyl-piperazine-1-carbonyl)-benzyl]-methyl-carbamic acid tert-butyl ester (212.5 mg, 0.40 mmol) in DCM (2 mL) was added TFA (1 mL). After 30 min, the mixture was concentrated and the residue was purified by FCC to give the desired product (119.3 mg, 69%). MS (ESI): mass calcd. for C22H27Cl2N3O2, 435.15; m/z found, 436.3 [M+H]+. 1H NMR (CDCl3): 7.50 (d, J=2.0, 1H), 7.38 (d, J=8.8, 1H), 7.30 (dd, J=8.3, 2.1, 1H), 7.06 (d, J=2.8, 1H), 6.88 (d, J=8.3, 1H), 6.82 (dd, J=8.8, 2.8, 1H), 3.81-3.69 (m, 4H), 3.53-3.37 (m, 2H), 2.78-2.68 (m, 1H), 2.64-2.43 (m, 4H), 2.43 (s, 3H), 1.93 (br s, 1H), 1.04 (d, J=6.5, 6H).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by FCC

Sources & evidence

ORD record
ord-446a516ca7654df79af12991b33cad51
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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