4-Chlorobenzoic Acid → 3-{3-[3-t-Butyl-5-(4-chloro-benzoylamino)-pyrazol-1-yl]-phenyl}-propionic acid ethyl ester

HRID 16962

反応式

HRID 16962 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14](=[O:33])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[C:27]([NH2:28])=[CH:26][C:25]([C:29]([CH3:32])([CH3:31])[CH3:30])=[N:24]2)[CH:18]=1)[CH3:12]>O=S(Cl)Cl.C(Cl)Cl>[CH2:11]([O:13][C:14](=[O:33])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[C:27]([NH:28][C:6](=[O:8])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[CH:26][C:25]([C:29]([CH3:32])([CH3:31])[CH3:30])=[N:24]2)[CH:18]=1)[CH3:12]

参加物

5

反応物 2

HCID 63184-Chlorobenzoic AcidHCID 58842892ethyl 3-(3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl)propanoate

生成物 1

HCID 588428933-{3-[3-t-Butyl-5-(4-chloro-benzoylamino)-pyrazol-1-yl]-phenyl}-propionic acid ethyl ester収率 64%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24386Thionyl Chloride溶媒

実験手順

A solution of 4-chlorobenzoic acid (312 mg, 2.0 mmol) in SOCl2 (10 mL) was heated to reflux for 2 h. After removal of the solvent, the residue was dissolved into CH2Cl2 (5 mL) and was dropped into a solution of Example Z (315 mg, 1.0 mmol) in CH2Cl2 (10 mL) at 0° C., was then stirred at RT overnight. After quenching with water (50 mL), the reaction mixture was extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with brine, dried (NaSO4) and filtered. After concentrated under reduced pressure, the residue was purified by flash chromatography to afford 3-{3-[3-t-butyl-5-(4-chloro-benzoylamino)-pyrazol-1-yl]-phenyl}-propionic acid ethyl ester (290 mg, 64%). 1H-NMR (CDCL3): 8.02 (s, 1H), 7.67 (d, J=8.4 Hz, 2H), 7.46 (t, J=7.6 Hz, 1H), 7.44 (d, J=8.4 Hz, 2H), 7.36 (t, J=8.4 Hz, 3H), 6.87 (s, 1H), 4.06 (q, J=7.6 Hz, 2H), 3.02 (t, J=7.6 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H), 1.40 (s, 9H), 1.12 (t, J=7.6 Hz, 3H); MS (ESI) m/z: 454 (M+H+).

後処理

  1. temperatureto reflux for 2 h
  2. customAfter removal of the solvent
  3. dissolutionthe residue was dissolved into CH2Cl2 (5 mL)
  4. customAfter quenching with water (50 mL)
  5. extractionthe reaction mixture was extracted with CH2Cl2 (3×100 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (NaSO4)
  8. filtrationfiltered
  9. concentrationAfter concentrated under reduced pressure
  10. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-2441b80b17dc4ec1a6681772e9efadf6
出典データセット
uspto-grants-2010_06
特許番号
US07737283B2

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