Potassium Carbonate → HCID 73505782, 화합물

HRID 1478585노트

반응식

HRID 1478585 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][N:15]3[C:19]4=[N:20][C:21]([C:24]5[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=5)=[CH:22][N:23]=[C:18]4[N:17]=[N:16]3)[CH2:9]2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1.[F:42][C:43]1[CH:55]=[C:54](B2OC(C)(C)C(C)(C)O2)[CH:53]=[CH:52][C:44]=1[CH2:45][N:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[F:42][C:43]1[CH:55]=[C:54]([C:2]2[CH:3]=[N:4][C:5]([N:8]3[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][N:15]4[C:19]5=[N:20][C:21]([C:24]6[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=6)=[CH:22][N:23]=[C:18]5[N:17]=[N:16]4)[CH2:9]3)=[N:6][CH:7]=2)[CH:53]=[CH:52][C:44]=1[CH2:45][N:46]1[CH2:47][CH2:48][O:49][CH2:50][CH2:51]1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 438110633-Fluoro-4-(N-morpholinomethyl)phenylboronic acid, pinacol esterHCID 73507291HCID 73507291, 화합물

생성물 1

HCID 73505782HCID 73505782, 화합물수율 111.2%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매

실험 절차

In a pressure tube reactor, (S)-4-(5-bromopyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine (40 mg, 0.08 mmol) was added, and then K2CO3 (36 mg, 0.26 mmol) was added. Pd(dppf)2Cl2 (4 mg, 0.004 mmol) was further added, and 1,4-dioxane (2 mL) and water (0.5 mL) were added. 4-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzyl)morpholine (42 mg, 0.13 mmol) was added, and then stirred at room temperature under nitrogen gas for 10 minutes, followed by stirring at 85° C. for 2 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate and water, and the extra water was removed by sodium sulfate, followed by concentration under reduced pressure. Column chromatography using 50% ethyl acetate/hexane gave (S)-4-(5-(3-fluoro-4-(morpholinomethyl)phenyl)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine (51 mg, 0.089 mmol) with a yield of 46%.

후처리

  1. stirringby stirring at 85° C. for 2 hours
  2. extractionthe organic layer was extracted with ethyl acetate and water
  3. customthe extra water was removed by sodium sulfate
  4. concentrationfollowed by concentration under reduced pressure

출처 및 근거

ORD 기록
ord-d996c77cc5ff44f3aef92d92c31f5fec
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403831B2

반응 노트

불러오는 중…