Thionyl Chloride → HCID 72203010, 화합물

HRID 629061

반응식

HRID 629061 반응식
[N:1]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=O)[CH:4]=[N:3][CH:2]=1.O=S(Cl)Cl.[F:20][C:21]([F:31])([F:30])[S:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>C(Cl)Cl>[N:3]1[CH:4]=[C:5]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([NH:27][C:26]2[CH:28]=[CH:29][C:23]([S:22][C:21]([F:31])([F:20])[F:30])=[CH:24][CH:25]=2)=[O:12])[CH:6]=[N:1][CH:2]=1

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 1230544-((Trifluoromethyl)thio)anilineHCID 41872503-Pyrimidin-5-yl-benzoic acid

생성물 1

HCID 72203010HCID 72203010, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 3-pyrimidin-5-yl-benzoic acid (100 mg, 0.50 mmol) and SOCl2 (73 μL, 1.0 mmol) was heated under reflux for 4 h. The solvent was evaporated off under reduced pressure and the residue was dissolved in DCM (5 mL) and slowly added to a mixture of 4-((trifluoromethyl)thio)aniline (106 mg, 0.55 mmol) and TEA (140 μL, 1.0 mmol) in DCM (5 mL). The mixture was stirred at RT overnight. The solvent was evaporated off under reduced pressure and the residue was suspended in EtOAc (10 mL), filtered through a 10 μm Isolute® fritted cartridge and the filtrate was evaporated to dryness under reduced pressure to give the crude product which was purified by preparative HPLC to afford the title compound. LC-MS (Condition 4) tR=1.19 min, m/z=375.9 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.67-7.78 (m, 3H) 7.93-8.02 (m, 2H) 8.04-8.10 (m, 2H) 8.38 (t, J=1.83 Hz, 1H) 9.21-9.29 (m, 3H) 10.63 (s, 1H).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. customThe solvent was evaporated off under reduced pressure
  4. dissolutionthe residue was dissolved in DCM (5 mL)
  5. customThe solvent was evaporated off under reduced pressure
  6. filtrationfiltered through a 10 μm Isolute® fritted cartridge
  7. customthe filtrate was evaporated to dryness under reduced pressure
  8. customto give the crude product which
  9. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-f8657e9625d14a4f930dc5e3a384e824
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315489B2

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