Sodium Carbonate → HCID 136217478, 화합물

HRID 1752428노트

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HRID 1752428 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11]([C@@H:14]([NH:16][C:17]1[N:22]=[C:21](Cl)[N:20]=[C:19]([C:24]([NH2:26])=[O:25])[CH:18]=1)[CH3:15])(=[O:13])[NH2:12].C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[C:11]([C@@H:14]([NH:16][C:17]1[N:22]=[C:21]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[N:20]=[C:19]([C:24]([NH2:26])=[O:25])[CH:18]=1)[CH3:15])(=[O:13])[NH2:12]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 89422280HCID 89422280, 화합물

생성물 1

HCID 136217478HCID 136217478, 화합물수율 91.6%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A 100 mL round-bottom flask was charged with 4-hydroxyphenyl boronic acid (1 g, 7.25 mmol), 6-((S)-1-carbamoyl-ethylamino)-2-chloro-pyrimidine-4-carboxylic acid amide (7.25 mmol, 1.76 g), PdCl2(PPh3)2 (Aldrich, 0.5 mmol, 0.3562 g), Na2CO3 (7.25 mL, 2M aqueous solution), and dioxane (5 mL). The flask was purged with nitrogen and heated to 100° C. for 16 h at which time the reaction was complete. The reaction mixture was concentrated under reduced pressure. The residue was suspended in 50% MeOH in DCM, filtered by vacuum, and the filter cake was discarded. The filtrate was concentrated under reduced pressure and was suspended in DCM, stirred for one hour, and filtered by vacuum filtration to provide the title compound as a light brown powder (2 g, 91%). 1H NMR (CD3OD) 8.25-8.09 (m, 2H), 7.09-6.92 (m, 1H), 6.82-6.70 (m, 2H), 4.62-4.40 (m, 1H), 1.49-1.31 (m, 3H). LC/MS: m/z 301[M+H]+.

후처리

  1. customThe flask was purged with nitrogen
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationfiltered by vacuum
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. filtrationfiltered by vacuum filtration

출처 및 근거

ORD 기록
ord-7b5bbcc73bdf44b39dc24999d09baabe
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163008B2

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