Diisopropylethylamine → HCID 59902279, 화합물

HRID 2230707노트

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HRID 2230707 반응식
I.I.[N:3]1([C:10]2[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:13]3[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=3[N:11]=2)[CH2:9][CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[N:35][N:34]=[N:33]2)=[CH:28][C:27]=1[C:37]([N:39]1[CH2:43][CH2:42][C@:41]([CH2:50][CH2:51]OS(C)(=O)=O)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:40]1)=[O:38].C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[N:35][N:34]=[N:33]2)=[CH:28][C:27]=1[C:37]([N:39]1[CH2:43][CH2:42][C@:41]([CH2:50][CH2:51][N:6]2[CH2:7][CH2:8][CH2:9][N:3]([C:10]3[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:13]4[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=4[N:11]=3)[CH2:4][CH2:5]2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:40]1)=[O:38]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 18464587HCID 18464587, 화합물HCID 86583904HCID 86583904, 화합물

생성물 1

HCID 59902279HCID 59902279, 화합물수율 19%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Heat a mixture of 2-[1,4]diazepan-1-yl-1-pentyl-1H-benzoimidazole dihydroiodide (0.83 g, 1.53 mmol), methanesulfonic acid 2-{(S)-1-[1-(2-methoxy-5-tetrazol-1-yl-phenyl)-methanoyl]-3-phenyl-pyrrolidin-3-yl}-ethyl ester (0.713 g, 1.51 mmol, example 47.2), diisopropylethylamine (1 mL, 5.74 mmol) and acetonitrile (15 mL) at 90° C. for 72 hours. Concentrate to dryness and dissolve the residue in dichloromethane. Wash the dichloromethane phase with NaHCO3 (10%, 10 mL) and brine (four 10 mL portions), dry (Na2SO4) the organic phase, filter and evaporate. Purify the residue by silica gel chromatography (3.5×35 cm) eluting with 95:5:0.05 dichloromethane:methanol:30% ammonium hydroxide solution. Concentrate the desired fractions to afford 0.19 g of the title compound, Rf=0.80 (silica gel, 90:10:0.1 dichloromethane:methanol:30% ammonium hydroxide solution). The product may be converted to the dihydrochloride by methods as are well known in the art.

후처리

  1. temperatureHeat
  2. concentrationConcentrate to dryness
  3. dissolutiondissolve the residue in dichloromethane
  4. washWash the dichloromethane phase with NaHCO3 (10%, 10 mL) and brine (four 10 mL portions)
  5. dry with materialdry (Na2SO4) the organic phase
  6. filtrationfilter
  7. customevaporate
  8. customPurify the residue by silica gel chromatography (3.5×35 cm)
  9. washeluting with 95:5:0.05 dichloromethane
  10. concentrationConcentrate the desired fractions

출처 및 근거

ORD 기록
ord-df212459ad124dbfbe36e527a04678ea
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06423704B1

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