2,6-Lutidine → HCID 59015783, 화합물

HRID 2113610노트

반응식

HRID 2113610 반응식
[CH2:1]([O:3][C:4](=[O:30])[CH:5](CCl)[CH2:6][C:7]1[N:16]=[C:15](O)[C:14]2[C:9](=[CH:10][C:11]([C:18]3[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:12][CH:13]=2)[N:8]=1)[CH3:2].O=P(Cl)(Cl)[Cl:33].N1C(C)=CC=CC=1C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][C:7]1[N:16]=[C:15]([Cl:33])[C:14]2[C:9](=[CH:10][C:11]([C:18]3[C:23]([C:24]([F:25])([F:27])[F:26])=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:12][CH:13]=2)[N:8]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 178471585HCID 178471585, 화합물

생성물 1

HCID 59015783HCID 59015783, 화합물

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

Reflux a mixture of 2-chloromethyl-3-[4-hydroxy-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-yl]-propionic acid ethyl ester (600 mg, 1.6 mmol), POCl3 (445 μl, 4.77 mmol), and 2,6-lutidine (596 μl, 4.77 mmol) in CHCl3 (20 ml) for 60 hours. Cool the mixture and concentrate under reduced pressure. Partition the residue between EtOAc and saturated NaHCO3 solution. Wash the EtOAc portion with additional NaHCO3 and then dry (Na2SO4) and concentrate under reduced pressure. Filter the brown residue through 2 inches of silica gel (1:1 EtOAc/hexanes eluent) and concentrate under reduced pressure to give 3-[4-chloro-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-yl]-propionic acid ethyl ester.

후처리

  1. temperatureReflux
  2. temperatureCool the mixture
  3. concentrationconcentrate under reduced pressure
  4. customPartition the residue between EtOAc and saturated NaHCO3 solution
  5. washWash the EtOAc portion with additional NaHCO3
  6. dry with materialdry (Na2SO4)
  7. concentrationconcentrate under reduced pressure
  8. filtrationFilter the brown residue through 2 inches of silica gel (1:1 EtOAc/hexanes eluent)
  9. concentrationconcentrate under reduced pressure

출처 및 근거

ORD 기록
ord-57ed9aa2f86d485c9c465933795e78bc
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432275B2

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