Ethyl acetate hexane → HCID 86724339, 화합물

HRID 1482683노트

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HRID 1482683 반응식
[F:1][C:2]1[C:3]([NH:21][C:22]2[CH:23]=[C:24]([NH:28]C(=O)OC(C)(C)C)[CH:25]=[CH:26][CH:27]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:11]([OH:20])[CH:10]=2)=[N:6][CH:7]=1.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[NH2:28][C:24]1[CH:23]=[C:22]([NH:21][C:3]2[C:2]([F:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:11]([OH:20])[CH:10]=3)[N:4]=2)[CH:27]=[CH:26][CH:25]=1

참가 물질

4

반응물 2

HCID 21226206Ethyl acetate hexaneHCID 86724338Tert-butyl (3-((5-fluoro-2-((3-hydroxy-4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate

생성물 1

HCID 86724339HCID 86724339, 화합물수율 91.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of tert-butyl (3-((5-fluoro-2-((3-hydroxy-4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate (0.240 g) in DCM (5.0 mL) TFA (2.0 mL) was added at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes followed by stirring at room temperature for 30 minutes. The reaction was monitored by TLC using ethyl acetate:hexane (7:3) as mobile phase. After completion of the reaction, the mixture was quenched in water and basified with saturated sodium bicarbonate solution. Product was extracted into DCM. The organic layer was washed with brine and dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. The obtained solid was purified by trituration with ether to give 0.175 g of 5-((4-((3-aminophenyl)amino)-5-fluoropyrimidin-2-yl)amino)-2-(2-methoxyethoxy)phenol. 1H NMR: DMSO-d6 (400 MHz): 3.282 (s, 3H), 3.617-3.640 (t, 2H, J=4.4), 4.004-4.040 (t, 2H, J=4.4), 4.992 (s, 2H), 6.306-6.316 (d, 1H, J=3.2), 6.772-6.793 (d, 1H, J=8.4), 6.952-7.042 (m, 3H), 7.095 (s, 1H), 7.187 (s, 1H), 8.004-8.013 (d, 1H, J=3.6), 8.811 (s, 1H), 8.861 (s, 1H), 9.001 (s, 1H).

후처리

  1. stirringby stirring at room temperature for 30 minutes
  2. customAfter completion of the reaction
  3. customthe mixture was quenched in water and basified with saturated sodium bicarbonate solution
  4. extractionProduct was extracted into DCM
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated completely
  8. customat 40° C
  9. customThe obtained solid was purified by trituration with ether

출처 및 근거

ORD 기록
ord-33bb41b3bc914b50a4de73acb894d791
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09415049B2

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