Dimethylformamide → HCID 58216598, compound

HRID 42369Notes

Reaction equation

HRID 42369 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)=O)[CH:6]=CC=CC=1.[Cl:28][C:29]1[N:34]=[C:33]([CH:35]=O)[C:32]([NH:37]C(=O)OC(C)(C)C)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C.O>[Cl:28][C:29]1[N:34]=[C:33]2[C:32](=[CH:31][CH:30]=1)[N:37]=[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]3([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:24])[CH3:25])[CH2:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=1)[C:7]([C:1]1[CH:8]=[CH:7][CH:1]=[CH:6][CH:6]=1)=[CH:35]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 57805516tert-Butyl {1-[4-(phenylacetyl)phenyl]cyclobutyl}carbamateHCID 58216578tert-Butyl (6-chloro-2-formylpyridin-3-yl)carbamate

Product 1

HCID 58216598HCID 58216598, 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 (6-chloro-2-formylpyridin-3-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-(6-chloro-3-phenyl-1,5-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-cb2a375574994237b62a87a93fcd5f83
Source dataset
uspto-grants-2013_09
Patent number
US08536193B2

Reaction notes

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