Trifluoroacetic acid → HCID 87191603, compound

HRID 2089021Notes

Reaction equation

HRID 2089021 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8]CC2C=CC(OC)=CC=2)[CH:5]=[C:4]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH:19]=2)[CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([S:27]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)(=[O:28])=[O:29])[CH:19]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 87191910HCID 87191910, compound

Product 1

HCID 87191603HCID 87191603, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of Example 150a (0.500 g, 0.990 mmol) in CH2Cl2 (9 mL) was added trifluoroacetic acid (4 mL, 51.9 mmol). The mixture was heated at 35° C. for 6 hours and concentrated. The residue was treated with saturated NaHCO3 and extracted with EtOAc. The organic layer was concentrated. The crude was triturated with EtOAc/diethyl ether to give 222 mg of the title compound. The filtrate was concentrated and purified on a 12 g column using the ISCO Companion flash system eluting with CH2Cl2/EtOAc (95:5 to 90:10) to give more title compound (84 mg).

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with saturated NaHCO3
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. customThe crude was triturated with EtOAc/diethyl ether

Sources & evidence

ORD record
ord-c17094e129d44ca788ca186d0013fe47
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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