Diisopropylethylamine → HCID 178461213, compound

HRID 81217Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a microwave vial was added (4aR,7aR)-octahydro-1H-cyclopenta[b]pyrazine (Preparative Example 5.2,295 mg, 2.338 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, 800 mg, 1.799 mmol), potassium fluoride (209 mg, 3.60 mmol), DMSO (8 ml), and DIEA (0.942 ml, 5.40 mmol). The reaction vial was capped and heated to 100° C. overnight. The mixture was then cooled to room temperature and diluted with EtOAc. The solution was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give crude 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(4aR,7aR)-octahydro-1H-cyclopenta[b]pyrazin-1-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc'd. for C27H32ClN7 [M+H]+ 490. found 490.

Workup

customThe reaction vial was capped
temperatureThe mixture was then cooled to room temperature
washThe solution was washed with water and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-f7c24fb0544f4accbbe4322981edbc39
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846657B2

Reaction notes

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