Water → 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(6-(5-(morpholine-4-carbonyl)pyridin-2-ylamino)pyrimidin-4-yl)benzyl acetate

HRID 402956노트

반응식

HRID 402956 반응식
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])=[CH:11][CH:10]=2)[CH:3]=1.[C:23]([O:26][CH2:27][C:28]1[C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][CH:31]=[CH:30][C:29]=1[N:43]1[N:52]=[CH:51][C:50]2[C:45](=[C:46]([F:57])[CH:47]=[C:48]([C:53]([CH3:56])([CH3:55])[CH3:54])[CH:49]=2)[C:44]1=[O:58])(=[O:25])[CH3:24].C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:53]([C:48]1[CH:49]=[C:50]2[C:45](=[C:46]([F:57])[CH:47]=1)[C:44](=[O:58])[N:43]([C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([C:2]3[CH:3]=[C:4]([NH:8][C:9]4[CH:10]=[CH:11][C:12]([C:15]([N:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)=[O:16])=[CH:13][N:14]=4)[N:5]=[CH:6][N:7]=3)[C:28]=1[CH2:27][O:26][C:23](=[O:25])[CH3:24])[N:52]=[CH:51]2)([CH3:54])([CH3:55])[CH3:56]

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 594737692-(6-(tert-Butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetateHCID 86686852HCID 86686852, 화합물

생성물 1

HCID 866868532-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(6-(5-(morpholine-4-carbonyl)pyridin-2-ylamino)pyrimidin-4-yl)benzyl acetate수율 30.7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a stirred solution of (6-(6-chloropyrimidin-4-ylamino)pyridin-3-yl)(morpholino)methanone (0.15 g, 0.45 mmol) in 1,4-dioxane (5 mL) was added 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate (0.250 g, 0.5 mmol), Pd(PPh3)4 (30 mg, 0.08 mmol), Na2CO3(212 mg, 2 mmol) and H2O (2 mL). The mixture was stirred at 80° C. for 13 hrs under N2. The mixture was evaporated and ethyl acetate (50 mL) and H2O (20 mL) were added to the resulting residue. The organic phase was washed with H2O (2×20 mL), brine (2×20 mL) and dried over Na2SO4. After filtration and concentration, the final product (90 mg, 30%) was obtained as yellow solid. LC-MS: 652.2 [M+H]+, tR=1.499 min.

후처리

  1. customThe mixture was evaporated
  2. additionethyl acetate (50 mL) and H2O (20 mL) were added to the resulting residue
  3. washThe organic phase was washed with H2O (2×20 mL), brine (2×20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration

출처 및 근거

ORD 기록
ord-88daa36b95fb47ba98704e1bf861e511
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742098B2

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