Dimethylformamide → HCID 57805456, compound

HRID 2104111Notes

Reaction equation

HRID 2104111 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:28][C:29]1[C:34]([CH:35]=O)=[C:33]([NH:37]C(=O)OC(C)(C)C)[CH:32]=[CH:31][N:30]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:35][C:34]4[C:33](=[CH:32][CH:31]=[N:30][C:29]=4[Cl:28])[N:37]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 52987944tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamateHCID 57805516tert-Butyl {1-[4-(phenylacetyl)phenyl]cyclobutyl}carbamate

Product 1

HCID 57805456HCID 57805456, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a round bottom flask was added tert-butyl{1-[4-(phenylacetyl)phenyl]cyclobutyl}carbamate (1-3) (2.7 g, 6.1 mmol), tert-butyl (2-chloro-3-formylpyridin-4-yl)carbamate (1-4) (1.6 g, 6.1 mmol), potassium carbonate (5.0 g, 6.0 mmol), and DMF (20 mL). The reaction mixture was heated to 80° C. while stirring in a hot oil bath under an atmosphere of nitrogen for 15 hours. Then the reaction mixture was warmed to 120° C. for 1 hour. The reaction mixture was permitted to cool to room temperature, added water, suspended in ethyl acetate, washed with a saturated solution of sodium bicarbonate, followed by water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (5-50% EtOAc/5% DCM/Hexane) to give tert-butyl{1-[4-(5-chloro-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate (1-5) as an off-white solid. HRMS (M+H)+: observed=486.1954, calculated=486.1943.

Workup

  1. temperatureThen the reaction mixture was warmed to 120° C. for 1 hour
  2. temperatureto cool to room temperature
  3. washwashed with a saturated solution of sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by silica gel chromatography (5-50% EtOAc/5% DCM/Hexane)

Sources & evidence

ORD record
ord-f06d715dee6a4306a648b16adeb21ec9
Source dataset
uspto-grants-2009_08
Patent number
US07576209B2

Reaction notes

Loading…