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

HRID 1471791노트

반응식

HRID 1471791 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-bf59f56b5e914ef9bcedf7c45f352e73
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012456B2

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