Ammonium Acetate → HCID 178502205, 화합물

HRID 1185728노트

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[CH3:1][O:2][C:3](=[O:32])[NH:4][CH:5]([C:9]([N:11]1[CH:15]([C:16](=O)[NH:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=2)=O)[CH2:14][N:13]([C:29](=[O:31])[CH3:30])[CH2:12]1)=[O:10])[CH:6]([CH3:8])[CH3:7].C([O-])(=O)C.[NH4+:37]>>[CH3:1][O:2][C:3](=[O:32])[NH:4][CH:5]([C:9]([N:11]1[CH:15]([C:16]2[NH:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=3)[N:37]=2)[CH2:14][N:13]([C:29](=[O:31])[CH3:30])[CH2:12]1)=[O:10])[CH:6]([CH3:8])[CH3:7]

참가 물질

반응물 2

HCID 517165Ammonium Acetate

HCID 66620312(1-{3-Acetyl-5-[2-(4-bromo-phenyl)-2-oxo-ethylcarbamoyl]-imidazolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

생성물 1

HCID 178502205HCID 178502205, 화합물수율 82.9%

반응 조건

온도: 135 °C

실험 절차

(1-{3-Acetyl-5-[2-(4-bromo-phenyl)-2-oxo-ethylcarbamoyl]-imidazolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (203 mg, 0.397 mmol) was dissolved in m-xylenes (4 mL) and heated at 135° C. Solid ammonium acetate (200 mg, 2.58 mmol) was added and the reaction was stirred at 135° C. After 120 minutes, the reaction was cooled to room temperature and the volatiles were removed in vacuo. The crude material was purified via silica gel chromatography (eluent: EtOAc w 10% MeOH/hexanes) to yield the product {1-[1′-Acetyl-4-(4-bromo-phenyl)-1′,2′,4′,5′-tetrahydro-1H-[2,4′]biimidazolyl-3′-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (162 mg, 0.329 mmol): LCMS-ESI+: calc'd for C21H26BrN5O4: 492.4 (M+). Found: 492.3/494.3 (M+H+).

후처리

temperaturethe reaction was cooled to room temperature
customthe volatiles were removed in vacuo
customThe crude material was purified via silica gel chromatography (eluent: EtOAc w 10% MeOH/hexanes)

출처 및 근거

ORD 기록: ord-14c14e7d7782472b96c75ca2864e5a4c
출처 데이터셋: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08669234B2

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