Triethylamine → 2-{3-[3-(1H-Benzotriazol-5-yl)-ureido]-2-oxo-7-phenyl-5-o-tolyl-azepan-1-yl}-N-tert-butyl-acetamide

HRID 429724노트

반응식

HRID 429724 반응식
[N:1]1[C:5]2=[CH:6][CH:7]=[C:8](C(O)=O)[CH2:9][C:4]2=[N:3][N:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])C=CC=CC=1.C([N:32]([CH2:35]C)CC)C.[C:37]([NH:41][C:42](=[O:66])[CH2:43][N:44]1[CH:50]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:49][CH:48]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[CH3:63])[CH2:47][CH:46]([NH2:64])[C:45]1=[O:65])([CH3:40])([CH3:39])[CH3:38]>O1CCCC1.C1C=CC=CC=1>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:32][C:35](=[O:20])[NH:64][CH:46]3[CH2:47][CH:48]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=4[CH3:63])[CH2:49][CH:50]([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[N:44]([CH2:43][C:42]([NH:41][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:66])[C:45]3=[O:65])=[CH:9][C:4]=2[N:3]=[N:2]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 15908914N-(t-Butyl)-2-oxo-3-amino-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amideHCID 534427314H-Benzo[d][1,2,3]triazole-5-carboxylic acid

생성물 1

HCID 1784241622-{3-[3-(1H-Benzotriazol-5-yl)-ureido]-2-oxo-7-phenyl-5-o-tolyl-azepan-1-yl}-N-tert-butyl-acetamide

시약·촉매·용매 2

HCID 241Benzene용매HCID 8028Tetrahydrofuran용매

실험 절차

To a 35 mL round-bottomed flank equipped with nitrogen inlet and condenser were added 40 mg (0.25 mmol) benzotriazole-5-carboxylic acid, 10 mL dry benzene, 10 mL dry tetrahydrofuran, 0.058 mL (0.27 mmol) diphenylphosphoryl azide, and 0.034 mL (0.27 mmol) triethylamine. The reaction was refluxed for 1.5 hour, cooled briefly, and 100 mg (0.25 mmol) N-(t-butyl)-2-oxo-3-amino-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-1-yl ethanoic amide (the more polar isomer from the preceding example) was added and refluxing continued for 10 hours. The reaction was cooled and evaporated the resulting residue was chromatographed on silica gel with methanol/methylene chloride as eluent to afford the title compound as a white amorphous solid, 53 mg (37%).

후처리

  1. customTo a 35 mL round-bottomed flank equipped with nitrogen inlet and condenser
  2. temperatureThe reaction was refluxed for 1.5 hour
  3. temperaturecooled briefly
  4. temperaturerefluxing
  5. temperatureThe reaction was cooled
  6. customevaporated the resulting residue
  7. customwas chromatographed on silica gel with methanol/methylene chloride as eluent

출처 및 근거

ORD 기록
ord-df9717887386411981caebee88efaea1
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06319915B1

반응 노트

불러오는 중…