Hexane → HCID 46215644, 화합물

HRID 2367173노트

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HRID 2367173 반응식
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:3]=1.O.[NH2:25][NH2:26].CCOC(C)=O.CCCCCC>CCO>[NH2:13][C:12]1[C:11]2[C:10](=[CH:9][C:8]([C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:5]=3)=[CH:15][CH:14]=2)[NH:26][N:25]=1

참가 물질

6

반응물 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 513565894-[2-Amino-6-(phenylamino)-4-pyrimidinyl]-2-fluorobenzonitrile

생성물 1

HCID 46215644HCID 46215644, 화합물수율 26.3%

시약·촉매·용매 1

HCID 702Ethanol용매2회

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온도
100 °C

실험 절차

To 4-[2-amino-6-(phenylamino)-4-pyrimidinyl]-2-fluorobenzonitrile (366 mg, 1.2 mmol) in EtOH (10 mL) was added hydrazine monohydrate (1.0 mL, 32 mmol) and the reaction mixture was stirred overnight at 100° C. The mixture was poured onto water and EtOAc. The layers were separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to afford crude product (230 mg). This material was dissolved in EtOH. Hexane was added until a precipitate began to form (a spatula was used to scratch the walls). The mixture was decanted and the solid was dried under vacuum to afford the title compound (100 mg, 26%) as a tan solid. LC-MS (ES) m/z=302, 304 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 6.51 (s, 1H), 7.04 (m, 1H), 7.32 (m, 2H), 7.46 (dd, J=8.6, 1.3 Hz, 1H), 7.66 (m, 2H), 7.75 (dd, J=8.3, 0.8 Hz, 1H), 7.81 (s, 1H).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was further extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford crude product (230 mg)
  8. customto form (a spatula
  9. customThe mixture was decanted
  10. customthe solid was dried under vacuum

출처 및 근거

ORD 기록
ord-de53a9fc66a34927851e63a7a31a8017
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697685B2

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