Diisopropylethylamine → HCID 178461244, compound

HRID 81191Notes

Reaction equation

HRID 81191 reaction equation
[F-].[K+].Br[C:4]1[N:21]([CH2:22][C@H:23]2[CH2:28][CH2:27][C@H:26]([CH3:29])[CH2:25][CH2:24]2)[C:7]2[C:8]([C:14]3[CH:15]=[N:16][CH:17]=[C:18]([Cl:20])[CH:19]=3)=[N:9][C:10]([C:12]#[N:13])=[CH:11][C:6]=2[N:5]=1.[NH:30]1[C:35](=[O:36])[CH2:34][NH:33][C@H:32]2[CH2:37][CH2:38][CH2:39][C@H:31]12.CCN(C(C)C)C(C)C>C(OCC)(=O)C.CS(C)=O>[Cl:20][C:18]1[CH:19]=[C:14]([C:8]2[C:7]3[N:21]([CH2:22][C@H:23]4[CH2:28][CH2:27][C@H:26]([CH3:29])[CH2:25][CH2:24]4)[C:4]([N:33]4[CH2:34][C:35](=[O:36])[NH:30][C@H:31]5[CH2:39][CH2:38][CH2:37][C@H:32]45)=[N:5][C:6]=3[CH:11]=[C:10]([C:12]#[N:13])[N:9]=2)[CH:15]=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 522689Potassium FluorideHCID 86724543(4aS,7aS)-octahydro-2H-cyclopenta[b]pyrazin-2-oneHCID 178461197HCID 178461197, compound

Product 1

HCID 178461244HCID 178461244, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A vial was charged with potassium fluoride (163 mg, 2.81 mmol), 2-bromo-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (Preparative Example 3.1, 250 mg, 0.562 mmol), (4aS,7aS)-octahydro-2H-cyclopenta[b]pyrazin-2-one (189 mg, 1.349 mmol), DMSO (1730 μl) and DIEA (491 μl, 2.81 mmol). The vial was capped and heated to 100° C. overnight. The mixture was then cooled to room temperature, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (0-20% MeOH in DCM) afforded 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(4aS,7aS)-3-oxooctahydro-1H-cyclopenta[b]pyrazin-1-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc'd. for C27H30ClN7O [M+H]+ 504. found 504.

Workup

  1. customThe vial was capped
  2. temperatureThe mixture was then cooled to room temperature
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (0-20% MeOH in DCM)

Sources & evidence

ORD record
ord-b13f3e42f00647aca60672636407e37a
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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