Water → HCID 86679610, 화합물

HRID 577663노트

반응식

HRID 577663 반응식
[F:1][C:2]1[C:10]2[C:9]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=3)=[N:8][C:7]([NH:21][C:22]3[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=3)=[N:6][C:5]=2[N:4]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:3]=1.[Cl-].[NH4+].O>CCOC(C)=O.C([O-])(O)=O.[Na+].[Zn]>[NH2:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][C:9]1[C:10]2[C:2]([F:1])=[CH:3][N:4]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:33])([CH3:34])[CH3:35])[C:5]=2[N:6]=[C:7]([NH:21][C:22]2[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=2)[N:8]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 86679608HCID 86679608, 화합물

생성물 1

HCID 86679610HCID 86679610, 화합물수율 81%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 8857Ethyl Acetate용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

A reaction vial was charged with 5-fluoro-N-(1-methyl-1H-pyrazol-3-yl)-4-(3-nitrophenoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (520 mg, 1.04 mmol), zinc dust (340 mg, 5.2 mmol), ammonium chloride (279 mg, 5.2 mmol), water (4 mL) and EtOAc (20 mL). The reaction mixture was capped and stirred at rt for 20 hrs. The reaction was diluted with EtOAc (100 mL) and saturated aqueous NaHCO3 (15 mL). The insoluble material was removed by filtration through Celite. The filtrate was separated, and the organic layer was washed with brine (10 mL), dried over Na2SO4 and evaporated to afford the title compound (394 mg, 81% yield) as a foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.52 (s, 1H) 7.45 (s, 1H) 7.26 (d, J=2.27 Hz, 1H) 7.14 (t, J=7.93 Hz, 1H) 6.49-6.59 (m, 2H) 6.46 (dd, J=7.93, 1.38 Hz, 1H) 6.30-6.43 (m, 1H) 5.50 (s, 2H) 5.32 (s, 2H) 3.75 (s, 3H) 3.56-3.67 (m, 2H) 0.89-0.98 (m, 2H) 0.00 (s, 9H). m/z (APCI+) for C22H28FN7O2Si 470.1 (M+H)+.

후처리

  1. customA reaction
  2. customThe reaction mixture was capped
  3. customThe insoluble material was removed by filtration through Celite
  4. customThe filtrate was separated
  5. washthe organic layer was washed with brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated

출처 및 근거

ORD 기록
ord-2950b4aa49734fc08bf94ed041e9f2da
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040547B2

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