Ammonium Chloride → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutanamide

HRID 218175ノート

反応式

HRID 218175 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([CH3:25])([CH3:24])[C:18]([CH3:23])([CH3:22])[C:19](O)=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[Cl-].[NH4+].O[N:29]1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C.C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([CH3:25])([CH3:24])[C:18]([CH3:23])([CH3:22])[C:19]([NH2:29])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

参加物

8

反応物 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 670063023-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutanoic acid

生成物 1

HCID 687047833-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutanamide収率 74%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred mixture of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutanoic acid (230 mg; 0.68 mmol), ammonium chloride (180 mg, 3.4 mmol), 1-hydroxy-7-azabenzotriazole (92 mg, 0.68 mmol), anhydrous acetonitrile (5 mL), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (325 mg, 1.7 mml) was added diisopropylethylamine (0.47 mL, 2.7 mmol). The mixture was stirred under nitrogen at rt for 22 hr before concentrated in vacuo. The residue was mixed with saturated aqueous sodium bicarbonate solution (15 mL) and extracted with dichloromethane (2×10 mL). The combined dichloromethane extracts were dried (Na2SO4). Flash chromatography (SiO2 Column, 10-100% ethyl acetate in hexanes) gave 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutanamide (169 mg, 0.50 mmol, 74% yield) as a white solid.

後処理

  1. concentrationbefore concentrated in vacuo
  2. additionThe residue was mixed with saturated aqueous sodium bicarbonate solution (15 mL)
  3. extractionextracted with dichloromethane (2×10 mL)
  4. dry with materialThe combined dichloromethane extracts were dried (Na2SO4)

出典と根拠

ORDレコード
ord-027168a0aad74b139f6c0738a22d0042
出典データセット
uspto-grants-2012_06
特許番号
US08198311B2

反応ノート

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