Cesium carbonate → HCID 67116748, compound

HRID 1193198Notes

Reaction equation

Br[C:2]1[C:3]([C:8]([N:10]2[CH2:17][CH2:16][C@@H:15]3[C@@H:12]([N:13]([C:18]4[N:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[N:19]=4)[CH2:14]3)[CH2:11]2)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[NH:26]1[CH:30]=[CH:29][N:28]=[N:27]1.C([O-])([O-])=O.[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.[Cu]I>[CH3:25][C:20]1[CH:21]=[C:22]([CH3:24])[N:23]=[C:18]([N:13]2[C@@H:12]3[C@@H:15]([CH2:16][CH2:17][N:10]([C:8]([C:3]4[C:2]([N:26]5[CH:30]=[CH:29][N:28]=[N:27]5)=[CH:7][CH:6]=[CH:5][N:4]=4)=[O:9])[CH2:11]3)[CH2:14]2)[N:19]=1

Participants

Conditions

Temperature: 160 °C

Procedure

The title compound was prepared by treating (1R,6S)-3-[(3-bromopyridin-2-yl)carbonyl]-8-(4,6-dimethylpyrimidin-2-yl)-3,8-diazabicyclo[4.2.0]octane (30 mg, 0.08 mmol), with 1H-1,2,3-triazole (43 uL, 0.75 mmol), Cs2CO3 (49 mg, 0.15 mmol), CuI (3.5 mg, 0.02 mmol), and (R,R)-(−)-N,N′-dimethyl-1,2-cyclohexanediamine (12 uL, 0.05 mmol) in 1,4-dioxane containing 3% water. The mixture was heated to 160° C. in a sealed tube. The reaction was purified directly on 16 g SiO2 with 0-2% NH3 MeOH/CH2Cl2 to give partially purified material which was further purified to the individual two isomers, the title compound (2 mg, 4% yield) and Example 183 (10 mg, 10% yield) by reverse phase HPLC. MS (ESI) mass calcd. for C20H22N8O, 390.5; m/z found, 391.2 [M+H]+.

Workup

customThe title compound was prepared
customThe reaction was purified directly on 16 g SiO2 with 0-2% NH3 MeOH/CH2Cl2
customto give partially purified material which
customwas further purified to the individual two isomers

Sources & evidence

ORD record: ord-9cbd742770ed45e1ae06a37fe9108c84
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680275B2

Reaction notes

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