Potassium Carbonate → HCID 86270813, compound

HRID 2177580Notes

Reaction equation

HRID 2177580 reaction equation
[CH3:1][C:2]1([CH3:17])[C:7]2[N:8]=[CH:9][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH2:5][CH2:4][NH:3]1.[Cl:18][C:19]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Cl:18][C:19]1[C:27]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([N:3]1[CH2:4][CH2:5][C:6]2[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:8][C:7]=2[C:2]1([CH3:17])[CH3:1])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 90409645HCID 90409645, compound

Product 1

HCID 86270813HCID 86270813, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 53, Step B (59 mg, 0.26 mmol) in DCM (2 mL) was added Intermediate 12 (63 mg, 0.26 mmol) and K2CO3 (89 mg, 0.65 mmol). The resulting suspension was stirred at room temperature for 2 h. The crude reaction mixture was filtered and concentrated and then purified on 12 g SiO2 column with 0-4% NH3/MeOH CH2Cl2 to give the desired compound (55 mg, 48%). MS (ESI): mass calcd. for C22H19ClF3N3O, 433.1. m/z found, 434.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.72 (dd, J=7.8, 1.4 Hz, 1H), 7.67 (s, 1H), 7.54-7.37 (m, 5H), 7.30 (dd, J=5.3, 3.3 Hz, 2H), 3.53-3.38 (m, 2H), 2.72-2.54 (m, 2H), 2.01 (d, J=6.3 Hz, 6H).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. custompurified on 12 g SiO2 column with 0-4% NH3/MeOH CH2Cl2

Sources & evidence

ORD record
ord-7617a5d36e89432798d60a2febfcbea1
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

Loading…