2,6-Lutidine → HCID 59015783、化合物

HRID 2113610ノート

反応式

HRID 2113610 の反応式
[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]

参加物

5

反応物 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 178471585HCID 178471585、化合物

生成物 1

HCID 59015783HCID 59015783、化合物

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-57ed9aa2f86d485c9c465933795e78bc
出典データセット
uspto-grants-2008_10
特許番号
US07432275B2

反応ノート

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