Hydrochloric Acid → HCID 11486614, 화합물

HRID 28584

반응식

HRID 28584 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[O:15][CH2:16][CH3:17])[N:5]=[C:4]([NH2:18])[N:3]=1.C(O)C.Cl.[O:23]1[C:27]([C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)=[CH:26][N:25]=[CH:24]1>O1CCOCC1>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH2:16][CH3:17])=[C:8]([C:6]2[N:5]=[C:4]([NH2:18])[N:3]=[C:2]([NH:34][C:31]3[CH:30]=[CH:29][C:28]([C:27]4[O:23][CH:24]=[N:25][CH:26]=4)=[CH:33][CH:32]=3)[CH:7]=2)[CH:13]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5177474-(1,3-Oxazol-5-yl)anilineHCID 860043254-Chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine

생성물 1

HCID 11486614HCID 11486614, 화합물수율 75%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a mixture of 4-chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine (100 mg, 0.37 mmol) and ethanol (20 ml) was added a solution of hydrogen chloride in 1,4-dioxane (4 M, 0.1 ml). After stirring for 10 minutes, 4-oxazol-5-yl-phenyl-amine (60 mg, 0.37 mmol) was added and the mixture was heated under reflux for 5 hours. After concentrating under reduced pressure, the residue was stirred with ethyl acetate (10 ml) and saturated aqueous sodium bicarbonate solution (10 ml). The solid was filtered and purified by flash chromatography eluting with ethyl acetate-hexane (1:1 followed by 3:2) to yield the title compound (110 mg, 75% yield). 1H NMR (acetone-d6) δ 1.44 (t, 3H, J=7.0 Hz, CH3), 4.17 (q, 2H, J=7.0 Hz, CH2), 5.88 (br s, 2H, NH), 7.04 (s, 1H, Ar), 7.12 (d, 1H, J=8.5 Hz, Ar), 7.37 (dd, 1H, J=8.8 Hz, J=2.9 Hz, Ar), 7.46 (s, 1H, Ar), 7.68 (d, 2H, J=8.7 Hz, Ar), 7.88-7.91 (m, 2H, Ar), 8.07 (d, 1H, J=2.8 Hz, Ar), 8.16 (s, 1H, Ar), 8.64 (br s, 1H, NH).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. concentrationAfter concentrating under reduced pressure
  4. stirringthe residue was stirred with ethyl acetate (10 ml) and saturated aqueous sodium bicarbonate solution (10 ml)
  5. filtrationThe solid was filtered
  6. custompurified by flash chromatography
  7. washeluting with ethyl acetate-hexane (1:1 followed by 3:2)

출처 및 근거

ORD 기록
ord-0a3f7d8513d24223b65530e0dd37c1e1
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

연결된 노트

불러오는 중…