Methyl 4-(1H-pyrazol-1-yl)benzoate → HCID 178490048, 화합물

HRID 16735노트

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HRID 16735 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 178490048HCID 178490048, 화합물

시약·촉매·용매 3

HCID 284Formic Acid용매HCID 1140Toluene용매HCID 6344Dichloromethane용매

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온도
82 °C

실험 절차

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+).

후처리

  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%)

출처 및 근거

ORD 기록
ord-dc8d6fc880db41ba83d41c5493bff1ee
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737149B2

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