Ethyl 3-{3-t-butyl-5-[3-(4-chlorophenyl)ureido]-1h-pyrazol-1-yl}benzoate → 1-{5-t-Butyl-2-[3-(1-hydroxy-1-methyl-ethyl)-phenyl]-2h-pyrazol-3-yl}-3-(4-chloro-phenyl)-urea

HRID 16979

反応式

HRID 16979 の反応式
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[O:12])[N:7]([C:21]2[CH:22]=[C:23]([CH:29]=[CH:30][CH:31]=2)C(OCC)=O)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Mg]Br.[C:35]1([CH3:41])C=CC=C[CH:36]=1.C1C[O:45]CC1>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:12])[N:7]([C:21]2[CH:31]=[CH:30][CH:29]=[C:23]([C:35]([OH:45])([CH3:41])[CH3:36])[CH:22]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 21867337Ethyl 3-{3-t-butyl-5-[3-(4-chlorophenyl)ureido]-1h-pyrazol-1-yl}benzoateHCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573、化合物

生成物 1

HCID 184498651-{5-t-Butyl-2-[3-(1-hydroxy-1-methyl-ethyl)-phenyl]-2h-pyrazol-3-yl}-3-(4-chloro-phenyl)-urea収率 81.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of Example C (220 mg, 0.5 mmol) in dry THF (20 mL) was added dropwise a solution of methyl magnesium bromide in toluene/THF (3.6 mL, 5.0 mmol) at −78° C. under N2. After stirring for 1 h, the mixture was allowed to rise to RT and stirred for another 2 h. The reaction mixture was quenched with saturated NH4Cl and aqueous HCl solution (10%), and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), the solvent was removed in vacuo and the residue was purified by column chromatography to afford 1-{5-t-butyl-2-[3-(1-hydroxy-1-methyl-ethyl)-phenyl]-2H-pyrazol-3-yl}-3-(4-chloro-phenyl)-urea (174 mg, 81%). 1H NMR (DMSO-d6): 9.11 (s, 1H), 8.34 (s, 1H), 7.59 (s, 1H), 7.46 (t, J=8.8 Hz, 1H), 7.43-7.40 (m, 3H), 7.31-7.28 (m, 3H), 6.34 (s, 1H), 5.13 (s, 1H), 1.42 (s, 6H), 1.27 (s, 9H); MS (ESI) m/z: 428 (M+H+).

後処理

  1. customto rise to RT
  2. stirringstirred for another 2 h
  3. customThe reaction mixture was quenched with saturated NH4Cl and aqueous HCl solution (10%)
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed in vacuo
  8. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-7c74fbbe13be42449700741559708bbe
出典データセット
uspto-grants-2010_06
特許番号
US07737283B2

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