Diisopropylethylamine → HCID 178461580, compound

HRID 81214Notes

Reaction equation

HRID 81214 reaction equation
[CH3:1][C@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.Br[C:16]1[N:33]([CH2:34][C@H:35]2[CH2:40][CH2:39][C@H:38]([CH3:41])[CH2:37][CH2:36]2)[C:19]2[C:20]([C:26]3[CH:27]=[N:28][CH:29]=[C:30]([Cl:32])[CH:31]=3)=[N:21][C:22]([C:24]#[N:25])=[CH:23][C:18]=2[N:17]=1.[F-].[K+].CCN(C(C)C)C(C)C>CCOC(C)=O.CS(C)=O>[Cl:32][C:30]1[CH:31]=[C:26]([C:20]2[C:19]3[N:33]([CH2:34][C@H:35]4[CH2:40][CH2:39][C@H:38]([CH3:41])[CH2:37][CH2:36]4)[C:16]([N:7]4[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][C@H:2]4[CH3:1])=[N:17][C:18]=3[CH:23]=[C:22]([C:24]#[N:25])[N:21]=2)[CH:27]=[N:28][CH:29]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 522689Potassium FluorideHCID 2756811(R)-1-Boc-3-methylpiperazineHCID 178461197HCID 178461197, compound

Product 1

HCID 178461580HCID 178461580, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a microwave vial was added (R)-tert-butyl 3-methylpiperazine-1-carboxylate (purchased from Astatech) (180 mg, 0.899 mmol), 2-bromo-4-(5-chloropyridin-3-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (200 mg, 0.450 mmol, Preparative Example 3.1), potassium fluoride (78 mg, 1.349 mmol), DMSO (1 ml) and DIEA (0.236 ml, 1.349 mmol). The reaction vial was capped and heated to 100° C. overnight. The mixture was cooled to room temperature and diluted with EtOAc. The mixture was washed with water and brine, then dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/isohexane to give (R)-tert-butyl 4-(4-(5-chloropyridin-3-yl)-6-cyano-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-2-yl)-3-methylpiperazine-1-carboxylate. MS ESI calc'd. for C30H38ClN7O2 [M+H]+ 564. found 564.

Workup

  1. customThe reaction vial was capped
  2. temperatureThe mixture was cooled to room temperature
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with EtOAc/isohexane

Sources & evidence

ORD record
ord-69eac9323d6e406ba8581aaf40dcbfca
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

Loading…