Dimethylformamide → 4-amino-N-[1-(2-fluoro-ethyl)-piperidin-4-yl]-3-methoxy-benzamide

HRID 1676520노트

반응식

HRID 1676520 반응식
N1(O[C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([O:19][CH3:20])[CH:13]=2)C2C=CC=CC=2N=N1.Cl.Cl.[F:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]1.CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O.O.C(N(CC)CC)C>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:33][CH:30]2[CH2:31][CH2:32][N:27]([CH2:26][CH2:25][F:24])[CH2:28][CH2:29]2)=[O:21])=[CH:13][C:14]=1[O:19][CH3:20]

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 106606854-Amino-3-methoxy-benzoic acid benzotriazol-1-yl esterHCID 866374991-(2-Fluoroethyl)piperidin-4-amine dihydrochloride

생성물 1

HCID 580151444-amino-N-[1-(2-fluoro-ethyl)-piperidin-4-yl]-3-methoxy-benzamide수율 73.7%

시약·촉매·용매 4

HCID 962Water용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

To a mixture of 0.5432 g (1.91 mmole) of 4-amino-3-methoxy-benzoic acid benzotriazol-1-yl ester, 0.4187 g (1.91 mmole) of 1-(2-fluoro-ethyl)-piperidin-4-ylamine dihydrochloride and 8 mL of dimethylformamide was added 1.3316 mL of triethylamine. The mixture was stirred for 25 hours, then taken up in ethyl acetate and twice with 50 mL 0.5 M sodium carbonate, once with 50 mL water, once with 50 mL brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with acetonitrile-methanol-triethylamine (90:10:0.8), to give 0.4159 g 4-amino-N-[1-(2-fluoro-ethyl)-piperidin-4-yl]-3-methoxy-benzamide.

후처리

  1. dry with materialdried over anhydrous sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with acetonitrile-methanol-triethylamine (90:10:0.8)

출처 및 근거

ORD 기록
ord-be396edbf58f42189ff16eb47261e2e7
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003785B2

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