Methyl 4-(1H-pyrazol-1-yl)benzoate → HCID 178490048、化合物

HRID 16735ノート

反応式

HRID 16735 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([NH2:20])[N:14](C(C)(C)C)[N:15]=2)[CH:6]=[CH:7][CH:8]=1.[N:21]1([C:26]2[CH:35]=[CH:34][C:29]([C:30](OC)=[O:31])=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[N:22]1.C[Al](C)C>C1(C)C=CC=CC=1.C(Cl)Cl.C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([NH:20][C:30](=[O:31])[C:29]3[CH:28]=[CH:27][C:26]([N:21]4[CH:25]=[CH:24][CH:23]=[N:22]4)=[CH:35][CH:34]=3)[NH:14][N:15]=2)[CH:6]=[CH:7][CH:8]=1

参加物

7

反応物 3

HCID 972639Methyl 4-(1H-pyrazol-1-yl)benzoateHCID 16682925TrimethylaluminumHCID 574539341-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-amine

生成物 1

HCID 178490048HCID 178490048、化合物

試薬・触媒・溶媒 3

HCID 284Formic Acid溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
82 °C

実験手順

5-[2-(3-Methoxyphenyl)ethyl]-2-tert-butyl-pyrazol-3-amine (0.2 g, 0.73 mmol) was dissolved in toluene (10 ml) and to this was added methyl 4-pyrazol-1-ylbenzoate (177 mg, 0.88 mmol) and AlMe3 (0.93 ml, 1.8 mmol). The reaction mixture was stirred overnight. The reaction mixture was diluted with DCM (15 ml), quenched with damp sodium sulfite and further stirred for 20 mins before being filtered. The solvent was removed in vacuo to yield a yellow gum. This gum was dissolved in formic acid (12 ml) and heated at 82° C. overnight. The reaction mixture was evaporated to dryness and the resulting product was passed through a SCX column, eluting initially with methanol followed by 2N ammonia/methanol. After solvent removal, a yellow solid was obtained which was triturated with hot acetonitrile to afford a white solid. The solid was filtered and dried (155 mg, 55%); 1H NMR (400.132 MHz, DMSO) δ 2.92 (s, 4H), 3.74 (s, 3H), 6.48 (s, 1H), 6.60 (s, 1H), 6.77 (d, 1H), 6.84-6.82 (m, 2H), 7.20 (t, 1H), 7.81 (s, 1H), 7.96 (d, 2H), 8.14 (d, 2H), 8.63 (s, 1H), 10.69 (s, 1H), 12.18 (s, 1H); MS: m/z 388 (MH+).

後処理

  1. customquenched with damp sodium sulfite
  2. stirringfurther stirred for 20 mins
  3. filtrationbefore being filtered
  4. customThe solvent was removed in vacuo
  5. customto yield a yellow gum
  6. customThe reaction mixture was evaporated to dryness
  7. washeluting initially with methanol
  8. customAfter solvent removal
  9. customa yellow solid was obtained which
  10. customwas triturated with hot acetonitrile
  11. customto afford a white solid
  12. filtrationThe solid was filtered
  13. customdried (155 mg, 55%)

出典と根拠

ORDレコード
ord-dc8d6fc880db41ba83d41c5493bff1ee
出典データセット
uspto-grants-2010_06
特許番号
US07737149B2

反応ノート

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