Diisopropylethylamine → HCID 178461213, 화합물

HRID 81217노트

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HRID 81217 반응식
[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

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 522689Potassium FluorideHCID 86724561(4aR,7aR)-octahydro-1H-cyclopenta[b]pyrazineHCID 178461197HCID 178461197, 화합물

생성물 1

HCID 178461213HCID 178461213, 화합물

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

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.

후처리

  1. customThe reaction vial was capped
  2. temperatureThe mixture was then cooled to room temperature
  3. washThe solution was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f7c24fb0544f4accbbe4322981edbc39
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846657B2

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