2-Naphthoic acid → 3-(3-{3-t-Butyl-5-[(naphthalene-2-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester

HRID 16960

反応式

HRID 16960 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.[CH2:14]([O:16][C:17](=[O:36])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]2[C:30]([NH2:31])=[CH:29][C:28]([C:32]([CH3:35])([CH3:34])[CH3:33])=[N:27]2)[CH:21]=1)[CH3:15]>O=S(Cl)Cl.C(Cl)Cl>[CH2:14]([O:16][C:17](=[O:36])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]2[C:30]([NH:31][C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[O:13])=[CH:29][C:28]([C:32]([CH3:35])([CH3:34])[CH3:33])=[N:27]2)[CH:21]=1)[CH3:15]

参加物

5

反応物 2

HCID 71232-Naphthoic acidHCID 58842892ethyl 3-(3-(3-t-butyl-5-amino-1H-pyrazol-1-yl)phenyl)propanoate

生成物 1

HCID 588429103-(3-{3-t-Butyl-5-[(naphthalene-2-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester収率 38.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24386Thionyl Chloride溶媒

実験手順

A solution of naphthalene-2-carboxylic acid (344 mg, 2.0 mmol) in SOCl2 (10 mL) was heated to reflux for 2 h. After concentration under reduced pressure, 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., and 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), filtered and concentrated under reduced pressure to yield a residue which was purified by flash chromatography to afford 3-(3-{3-t-butyl-5-[(naphthalene-2-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester (180 mg, 38%). 1H-NMR (CDCL3): 8.24 (s, 1H), 8.21 (s, 1H), 7.91 (d, J=8.4 Hz, 2H), 7.88 (d, J=8.4 Hz, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.63-7.49 (m, 3H), 7.45-7.26 (m, 3H), 6.94 (s, 1H), 4.02 (q, J=7.2 Hz, 2H), 3.04 (t, J=7.6 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H), 1.43 (s, 9H), 1.17 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 470 (M+H+).

後処理

  1. temperatureto reflux for 2 h
  2. concentrationAfter concentration under reduced pressure
  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. concentrationconcentrated under reduced pressure
  10. customto yield a residue which
  11. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-9b678a5b4b0246ca9cc2852fe412914a
出典データセット
uspto-grants-2010_06
特許番号
US07737283B2

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