Trifluoroacetic acid → HCID 131728089, compound

HRID 1512366Notes

Reaction equation

HRID 1512366 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]2[C:27]([CH2:28][NH:29][C:30]3[N:34]([C:35]4[CH:40]=[CH:39][C:38]([F:41])=[C:37]([Cl:42])[C:36]=4[Cl:43])[N:33]=[N:32][N:31]=3)=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[C:3]([OH:5])(=[O:4])[CH3:2].[C:3]([OH:5])(=[O:4])[CH3:2].[N:18]1([C:22]2[C:27]([CH2:28][NH:29][C:30]3[N:34]([C:35]4[CH:40]=[CH:39][C:38]([F:41])=[C:37]([Cl:42])[C:36]=4[Cl:43])[N:33]=[N:32][N:31]=3)=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:19][CH2:20][CH2:21][NH:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68583891HCID 68583891, compound

Product 1

HCID 131728089HCID 131728089, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to a solution of the product of Example 288C (0.40 g, 0.744 mmol) in dichloromethane (15 mL) at 0° C. 5 minutes later, the ice bath was removed and the reaction mixture was stirred at room temperature for 16 hours. The solvent was removed and the residue was purified by preparative HPLC on a Thermoquest, hyperprep HS C18 column (250×21.2 mm., 8 μm particle size) using a gradient of 5% to 75% acetonitrile to ammonium acetate (10 mM) over 20 minutes at a flow rate of 21 mL/min to provide the title compound. MS (ESI+) m/z 437.3 (M+H)+; Rt=1.41 min. 1H-NMR (400 MHz, DMSO-d6) δ 1.78 (m, 2H), 1.98 (s, 6H), 2.84 (m, 2H), 2.90 (m, 2H), 3.38 (m, 4H), 4.46 (d, J=5.1 Hz, 2H), 6.85 (dd, J=4.8 Hz, J=7.5 Hz, 1H), 7.53 (dd, J=1.9 Hz, J=7.5 Hz, 1H), 7.61 (t, J=5.6 Hz, 1H), 7.74 (t, J=8.8 Hz, 1H), 7.86 (dd, J=5.3 Hz, J=9.0 Hz, 1H), 8.08 (dd, J=1.9 Hz, J=4.8 Hz, 1H).

Workup

  1. custom5 minutes later, the ice bath was removed
  2. customThe solvent was removed
  3. customthe residue was purified by preparative HPLC on a Thermoquest, hyperprep HS C18 column (250×21.2 mm., 8 μm particle size)
  4. customover 20 minutes

Sources & evidence

ORD record
ord-82e1f89433674b698f6b849d4d2be332
Source dataset
uspto-grants-2012_07
Patent number
US08217067B2

Reaction notes

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