Sodium Iodide → 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(2-(trifluoromethoxy)ethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

HRID 323514노트

반응식

HRID 323514 반응식
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:26]([N:29]2[CH:33]=[N:32][N:31]=[N:30]2)=[CH:25][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:12][CH2:13]OS(C)(=O)=O)[CH2:8]1)=[O:6].[F:34][C:35]([F:56])([F:55])[O:36][CH2:37][CH2:38][N:39]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[N:41]=[C:40]1[NH:48][CH:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1.C(N(CC)CC)C.[I-].[Na+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:26]([N:29]2[CH:33]=[N:32][N:31]=[N:30]2)=[CH:25][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([CH2:12][CH2:13][N:52]2[CH2:53][CH2:54][CH:49]([NH:48][C:40]3[N:39]([CH2:38][CH2:37][O:36][C:35]([F:56])([F:34])[F:55])[C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=4[N:41]=3)[CH2:50][CH2:51]2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:8]1)=[O:6]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 184648112-methoxy-5-(1H-tetrazol-1-yl)benzoyl-3-phenyl-3-(2-methanesulfonyloxyethyl)-pyrrolidineHCID 22009402(1-(2-(trifluoromethoxy)ethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine

생성물 1

HCID 99181451-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(2-(4-(1-(2-(trifluoromethoxy)ethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Combine 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (prepared from (−)-3-(2-hydroxyethyl)-3-phenylpyrrolidine (R,R)-di-p-anisoyltartaric acid salt) (0.86 g, 1.83 mmol), (1-(2-(trifluoromethoxy)ethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydrochlorici acid salt (1.66 mmol), triethylamine (1.0 mL, 7.2 mmol), and sodium iodide (0.31 g) in acetonitrile (24 mL). Heat to reflux. After 48 hours, evaporate in vacuo to give a residue. Partition the residue between dichloromethane and a saturated aqueous sodium, bicarbonate solution. Separate the layers and extract the organic layer with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

후처리

  1. temperatureHeat to reflux
  2. customevaporate in vacuo
  3. customto give a residue
  4. customPartition the residue between dichloromethane
  5. customSeparate the layers
  6. extractionextract the organic layer with a saturated aqueous sodium bicarbonate solution
  7. dry with materialDry the organic layer over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-9b8a5e0aa3f14d1785d7981924aa7ebc
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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