Tetrahydrofuran → Methyl 5-formyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate

HRID 1741627노트

반응식

HRID 1741627 반응식
C([N:9]1[C:13](=[O:14])[C:12]([CH:16]([CH3:18])[CH3:17])([CH3:15])[N:11]=[C:10]1[C:19]1[N:28]=[CH:27][C:26](C(Br)Br)=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])(=O)C1C=CC=CC=1.C(NCCN)C.C(N(CC)CC)C.[O:45]1CCC[CH2:46]1>>[CH:46]([C:26]1[CH:27]=[N:28][C:19]([C:10]2[NH:9][C:13](=[O:14])[C:12]([CH:16]([CH3:17])[CH3:18])([CH3:15])[N:11]=2)=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22])=[O:45]

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 8471TriethylamineHCID 66071N-Ethylethylenediamine2회HCID 867480372-(1-Benzoyl-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-(dibromomethyl)nicotinic acid, methyl ester

생성물 1

HCID 15676632Methyl 5-formyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate

실험 절차

A stirred solution of 1.38 g of 2-(1-benzoyl-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-(dibromomethyl)nicotinic acid, methyl ester, in 35 mL tetrahydrofuran is cooled to -78° and treated with a mixture of 0.3 mL of N-ethylethylenediamine, 10 mL tetrahydrofuran, and 0.8 mL of triethylamine. After warming to room temperature, the reaction solution is treated with 0.3 mL of N-ethylethylenediamine, stirred for 2 hours, heated at reflux for 24 hours, and concentrated in vacuo. The residue is partitioned between methylene chloride and water; the aqueous phase is further extracted with methylene chloride, and the combined organic phases are dried and concentrated in vacuo. Chromatography of the residue on silica gel using hexane-ethyl acetate mixtures affords the desired product, mp 113°-117°.

후처리

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. concentrationconcentrated in vacuo
  4. customThe residue is partitioned between methylene chloride and water
  5. extractionthe aqueous phase is further extracted with methylene chloride
  6. customthe combined organic phases are dried
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-99ab6b35aaf0408391f731c883836ce4
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334576

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