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

HRID 1676520ノート

反応式

HRID 1676520 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-be396edbf58f42189ff16eb47261e2e7
出典データセット
uspto-grants-2011_08
特許番号
US08003785B2

反応ノート

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