Isopropyl chloroformate → 4-[5-(2-Fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid isopropyl ester

HRID 1471791ノート

反応式

HRID 1471791 の反応式
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[F:8][C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:19]1[CH:20]=[C:21]2[CH:27]=[C:26]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[O:25][C:22]2=[CH:23][N:24]=1.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH:5]([O:4][C:2]([N:31]1[CH2:32][CH2:33][CH:28]([C:26]2[O:25][C:22]3=[CH:23][N:24]=[C:19]([C:10]4[CH:11]=[CH:12][C:13]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:14][C:9]=4[F:8])[CH:20]=[C:21]3[CH:27]=2)[CH2:29][CH2:30]1)=[O:3])([CH3:7])[CH3:6]

参加物

5

反応物 3

HCID 7917Isopropyl chloroformateHCID 81531DiisopropylethylamineHCID 866945755-(2-Fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine

生成物 1

HCID 717367234-[5-(2-Fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid isopropyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Isopropyl chloroformate (1 mol/L in toluene; 0.30 mL) is added to a solution of 5-(2-fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine (75 mg) and N,N-diisopropyl-ethylamine (0.10 mL) in tetrahydrofuran (1 mL) chilled in an ice bath. The solution is stirred at room temperature for 3 h. The solution is concentrated and the residue is taken up in water and dichloromethane. The resulting mixture is extracted with dichloromethane and the combined extracts are dried (Na2SO4). The solvent is evaporated and the residue is purified by HPLC on reversed phase (methanol/water) to give the title compound. Mass spectrum (ESI+): m/z=461 [M+H]+.

後処理

  1. temperaturechilled in an ice bath
  2. concentrationThe solution is concentrated
  3. extractionThe resulting mixture is extracted with dichloromethane
  4. dry with materialthe combined extracts are dried (Na2SO4)
  5. customThe solvent is evaporated
  6. customthe residue is purified by HPLC on reversed phase (methanol/water)

出典と根拠

ORDレコード
ord-bf59f56b5e914ef9bcedf7c45f352e73
出典データセット
uspto-grants-2015_04
特許番号
US09012456B2

反応ノート

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