Trifluoroacetic acid → HCID 131728091, compound

HRID 645668Notes

Reaction equation

HRID 645668 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[C:26]([CH2:27][NH:28][C:29]3[N:33]([C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=4[Cl:41])[N:32]=[N:31][N:30]=3)=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[C:3]([OH:5])(=[O:4])[CH3:2].[Cl:41][C:35]1[C:36]([Cl:40])=[CH:37][CH:38]=[CH:39][C:34]=1[N:33]1[C:29]([NH:28][CH2:27][C:26]2[C:21]([N:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)=[N:22][CH:23]=[CH:24][CH:25]=2)=[N:30][N:31]=[N:32]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68680237HCID 68680237, compound

Product 1

HCID 131728091HCID 131728091, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (45 mL) was added to a solution of Example 315C (5.72 g, 11.32 mmol) in dichloromethane (220 mL) at 0° C. After 5 minutes, the ice bath was removed and the reaction mixture was stirred at room temperature for 16 hours. The residue was partitioned between dichloromethane and 1.0 N sodium hydroxide. The organic 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 405.4 (M+H)+; Rt=1.37 min. 1H-NMR (400 MHz, DMSO-d6) δ 8.180 (m, 1H); 7.942 (m, 1H); 7.728 (m, 1H); 7.668 (m, 1H); 7.612 (m, 2H); 7.000 (m, 1H); 4.498 (m, 2H); 2.961 (m, 4H); 2.842 (m, 4H); 1.891 (m, 3H).

Workup

  1. customthe ice bath was removed
  2. customThe residue was partitioned between dichloromethane and 1.0 N sodium hydroxide
  3. customThe organic solvent was removed
  4. customthe residue was purified by preparative HPLC on a Thermoquest, hyperprep HS C18 column (250×21.2 mm., 8 μm particle size)
  5. customover 20 minutes

Sources & evidence

ORD record
ord-1970c941c9ba47a49cb3ab7c490f085e
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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