Diisopropylethylamine → HCID 59902279、化合物

HRID 2230707ノート

反応式

HRID 2230707 の反応式
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]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 18464587HCID 18464587、化合物HCID 86583904HCID 86583904、化合物

生成物 1

HCID 59902279HCID 59902279、化合物収率 19%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-df212459ad124dbfbe36e527a04678ea
出典データセット
uspto-grants-2002_07
特許番号
US06423704B1

反応ノート

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