Potassium Carbonate → HCID 58034515, compound

HRID 1914821Notes

Reaction equation

[Cl:1][C:2]1[C:7]([NH:8]C(=O)OC(C)(C)C)=[C:6]([CH:16]=O)[CH:5]=[CH:4][N:3]=1.[C:18]1([CH2:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=2)=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[N:8]=[C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]3([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:43])[CH3:41])[CH2:34][CH2:35][CH2:36]3)=[CH:29][CH:28]=1)[C:24]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[CH:16]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of tert-butyl (2-chloro-4-formylpyridin-3-yl)carbamate (7-3) (300 mg, 1.17 mmol), tert-butyl {1-[4-(phenylacetyl)phenyl]cyclobutyl}carbamate (4-1) (427 mg, 1.17 mmol) and potassium carbonate (485 mg, 3.51 mmol) in DMF (10 mL) was stirred at 120° C. for 15 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane-EtOAc) to give tert-butyl {1-[4-(8-chloro-3-phenyl-1,7-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate (7-4) as a pale yellow solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (hexane-EtOAc)

Sources & evidence

ORD record: ord-66d1d7325bce42c9a4f85efebaa68ca5
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614221B2

Reaction notes

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