Diisopropylethylamine → 4-[5-(2-Fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid 1-methyl-cyclopropyl ester

HRID 1471792노트

반응식

HRID 1471792 반응식
[C:1](=[O:17])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][C:3]1([CH3:6])[CH2:5][CH2:4]1.[F:18][C:19]1[CH:24]=[C:23]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:22]=[CH:21][C:20]=1[C:29]1[CH:30]=[C:31]2[CH:37]=[C:36]([CH:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)[O:35][C:32]2=[CH:33][N:34]=1.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH3:6][C:3]1([O:2][C:1]([N:41]2[CH2:42][CH2:43][CH:38]([C:36]3[O:35][C:32]4=[CH:33][N:34]=[C:29]([C:20]5[CH:21]=[CH:22][C:23]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:24][C:19]=5[F:18])[CH:30]=[C:31]4[CH:37]=3)[CH2:39][CH2:40]2)=[O:17])[CH2:4][CH2:5]1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 579301151-Methylcyclopropyl 4-nitrophenyl carbonateHCID 866945755-(2-Fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine

생성물 1

HCID 717367244-[5-(2-Fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid 1-methyl-cyclopropyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1-Methyl-cyclopropyl 4-nitrophenyl carbonate (48 mg) 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 (32 μL) in tetrahydrofuran (1 mL) at room temperature. The mixture is stirred at room temperature overnight. The solution is concentrated and the residue is taken up in ethyl acetate. The resulting mixture is washed with 1 M aqueous NaOH solution (3×), water, and brine. The organic phase is dried (Na2SO4) and concentrated. The residue is purified by HPLC on reversed phase (methanol/water) to give the title compound. Mass spectrum (ESI+): m/z=473 [M+H]+.

후처리

  1. concentrationThe solution is concentrated
  2. washThe resulting mixture is washed with 1 M aqueous NaOH solution (3×), water, and brine
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue is purified by HPLC on reversed phase (methanol/water)

출처 및 근거

ORD 기록
ord-64e431bc24704ea88cdd91832ab2150b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012456B2

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