Methanesulfonyl chloride → 2-{7-[(3,4-Difluorophenyl)methoxy]-1,5-naphthyridin-3-yl}acetonitrile

HRID 1748412ノート

反応式

HRID 1748412 の反応式
CS(O[CH2:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[N:14][CH:13]=[C:12]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)[CH:11]=2)(=O)=O.FC1C=C(C=CC=1F)COC1C=C2C(C=C(CO)C=N2)=[N:35][CH:34]=1.CS(Cl)(=O)=O>C(Cl)Cl>[F:26][C:21]1[CH:20]=[C:19]([CH2:18][O:17][C:12]2[CH:11]=[C:10]3[C:15]([CH:16]=[C:7]([CH2:6][C:34]#[N:35])[CH:8]=[N:9]3)=[N:14][CH:13]=2)[CH:24]=[CH:23][C:22]=1[F:25]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 86301659(7-((3,4-Difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methanolHCID 90418375(7-((3,4-Difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methyl methanesulfonate

生成物 1

HCID 863016602-{7-[(3,4-Difluorophenyl)methoxy]-1,5-naphthyridin-3-yl}acetonitrile収率 64%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(7-((3,4-difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methyl methanesulfonate. To a solution of (7-((3,4-difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methanol (Example 73, 90 mg, 0.3 mmol) in DCM (4 mL) was added methanesulfonyl chloride (0.05 mL, 0.61 mmol) followed by TEA (0.06 mL, 0.43 mmol). The reaction mixture was stirred at RT for 1 h and quenched with saturated NaHCO3 solution. The mixture was extracted with DCM (2×) and the combined organic layers were dried, filtered and concentrated under reduced pressure. Purification (FCC, SiO2, 0-80%, EtOAc/hexanes) afforded the title compound as a white solid (73 mg, 64%). [M+H]=381.1.

後処理

  1. customquenched with saturated NaHCO3 solution
  2. extractionThe mixture was extracted with DCM (2×)
  3. customthe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification (FCC, SiO2, 0-80%, EtOAc/hexanes)

出典と根拠

ORDレコード
ord-8d7cd42cd04b41eb8847ef2ddfc9f335
出典データセット
uspto-grants-2015_10
特許番号
US09150572B2

反応ノート

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