Hydrochloric Acid → HCID 71251917, compound

HRID 2202158Notes

Reaction equation

HRID 2202158 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[N:10]([C:19]3[N:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:27][C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:29])[CH2:15][CH2:14]3)[N:10]([C:19]3[N:20]=[CH:21][CH:22]=[CH:23][N:24]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 71252032HCID 71252032, compound

Product 1

HCID 71251917HCID 71251917, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of INTERMEDIATE 9 HCl salt (72.4 mg, 0.17 mmol) in DMF (1.0 ml) was added 2-bromoacetophenone (83.0 mg, 0.42 mmol), followed by the portionwise addition of potassium carbonate (138.0 mg, 1.00 mmol). After stirring at ambient temperature overnight, the reaction mixture was quenched with a saturated solution of ammonium chloride, extracted with EtOAc, and washed with water and brine. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified using a silica gel cartridge using a gradient of 0-50% ethyl acetate in hexanes, followed by a gradient of 0-10% methanol in dichloromethane to give the title compound as a yellow oil, which solidified on standing. LC-MS (m/z): 443.10 [M+H]+. 1H NMR (CDCl3, 500 MHz): δ 8.92 (d, J=4.8 Hz, 2H), 8.25-8.27 (in, 2H), 8.10 (d, J=8.1 Hz, 2H), 7.60-7.62 (m, 1H), 7.50 (t, J=7.6 Hz, 2H), 7.37 (t, J=4.8 Hz, 1H), 7.15 (t, J=8.6 Hz, 2H), 3.88 (s, 2H), 3.80-3.86 (in, 1H), 3.13-3.15 (br, 2H), 2.41-2.45 (br, 2H), 2.07-2.27 (br, 4H).

Workup

  1. customthe reaction mixture was quenched with a saturated solution of ammonium chloride
  2. extractionextracted with EtOAc
  3. washwashed with water and brine
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified

Sources & evidence

ORD record
ord-1ac211083079490993c8b1d64140d392
Source dataset
uspto-grants-2016_06
Patent number
US09365539B2

Reaction notes

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