4-Methylmorpholine → N-(2-dimethylaminoethyl)-2-oxo-3-(2-oxo-2,3-dihydro-1H-benzimidazol-5-ylmethyl)-2,3-dihydrobenzoxazole-5-carboxamide

HRID 1970867노트

반응식

HRID 1970867 반응식
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:17]=[CH:16][C:11]3[NH:12][C:13](=[O:15])[NH:14][C:10]=3[CH:9]=2)[C:5]2[CH:18]=[C:19]([C:22]([OH:24])=O)[CH:20]=[CH:21][C:4]=2[O:3]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[CH3:53][N:54]([CH3:58])[CH2:55][CH2:56][NH2:57]>CN(C=O)C.O>[CH3:53][N:54]([CH3:58])[CH2:55][CH2:56][NH:57][C:22]([C:19]1[CH:20]=[CH:21][C:4]2[O:3][C:2](=[O:1])[N:6]([CH2:7][C:8]3[CH:17]=[CH:16][C:11]4[NH:12][C:13](=[O:15])[NH:14][C:10]=4[CH:9]=3)[C:5]=2[CH:18]=1)=[O:24]

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 595647202-oxo-3-(2-oxo-2,3-dihydro-1H-benzimidazol-5-ylmethyl)-2,3-dihydrobenzoxazole-5-carboxylic acid

생성물 1

HCID 59564717N-(2-dimethylaminoethyl)-2-oxo-3-(2-oxo-2,3-dihydro-1H-benzimidazol-5-ylmethyl)-2,3-dihydrobenzoxazole-5-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

330 mg (0.76 mmol) of 2-oxo-3-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl-methyl)-2,3-dihydrobenzoxazole-5-carboxylic acid are dissolved in 3 ml of DMF, and 294 mg (1.52 mmol) of EDCI, 106 mg (0.76 mmol) of HOBt and 157 μl (1.52 mmol) of N-methylmorpholine are added. 81 mg (0.91 mmol) of 2-dimethylaminoethylamine are subsequently added, and the reaction solution is stirred at room temperature for 3 days. The reaction mixture is subsequently added to water and extracted with dichloromethane. The organic phase is dried over sodium sulfate, evaporated to dryness and purified by column chromatography on silica gel. The product is purified again by preparative HPLC; 100 mg of “A35” trifluoromethylacetate; ESI 397 (M+H), HPLC: Rt=3.89 min (method A).

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated to dryness
  4. custompurified by column chromatography on silica gel
  5. customThe product is purified again by preparative HPLC

출처 및 근거

ORD 기록
ord-efb10128de8141e9a96c7fcc2846bc5b
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431572B2

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