Diisopropylethylamine → Tert-butyl (2S)-2-{[4-(methylamino)phenyl]carbonylamino}-4-(N-{2-[2-(2-{2-[2-(4-{5-[(N-morpholin-4-ylcarbamoyl)amino]-4-oxoindeno[3,2-c]pyrazol-3-yl}phenoxy)acetylamino]ethoxy}ethoxy)ethoxy]ethyl}carbamoyl)butanoate

HRID 720867노트

반응식

HRID 720867 반응식
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][C:14]([CH2:16][CH2:17][C@H:18]([NH:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([N:35](C(OCC2C=CC=CC=2)=O)[CH3:36])=[CH:31][CH:30]=1)=[O:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:15].[N:47]1([NH:53][C:54]([NH:56][C:57]2[C:62]3[C:63](=[O:80])[C:64]4[C:65](=[N:66][NH:67][C:68]=4[C:69]4[CH:79]=[CH:78][C:72]([O:73][CH2:74][C:75](O)=[O:76])=[CH:71][CH:70]=4)[C:61]=3[CH:60]=[CH:59][CH:58]=2)=[O:55])[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:36][NH:35][C:32]1[CH:31]=[CH:30][C:29]([C:27]([NH:26][C@@H:18]([CH2:17][CH2:16][C:14](=[O:15])[NH:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:75](=[O:76])[CH2:74][O:73][C:72]2[CH:71]=[CH:70][C:69]([C:68]3[NH:67][N:66]=[C:65]4[C:61]5[CH:60]=[CH:59][CH:58]=[C:57]([NH:56][C:54](=[O:55])[NH:53][N:47]6[CH2:48][CH2:49][O:50][CH2:51][CH2:52]6)[C:62]=5[C:63](=[O:80])[C:64]=34)=[CH:79][CH:78]=2)[C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])=[O:28])=[CH:34][CH:33]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66910315HCID 66910315, 화합물HCID 1785259502-(4-(5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-3-yl}phenoxy)acetic Acid

생성물 1

HCID 178482176Tert-butyl (2S)-2-{[4-(methylamino)phenyl]carbonylamino}-4-(N-{2-[2-(2-{2-[2-(4-{5-[(N-morpholin-4-ylcarbamoyl)amino]-4-oxoindeno[3,2-c]pyrazol-3-yl}phenoxy)acetylamino]ethoxy}ethoxy)ethoxy]ethyl}carbamoyl)butanoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Compound 12 (0.71 g, 1.4 mmol) and compound 25 (0.57 g, 1.2 mmol) were dissolved in 10 ml DMF and HBTU (0.8 g, 2.1 mmol) was added as a solid followed by DIEA (0.52 ml, 3 mmol). The reaction mixture was stirred at room temperature for 3 days, diluted with EtOAc and the organic phase washed with saturated NaHCO3. The aqueous layer was back extracted with EtOAc twice and the combined organic layers dried over MgSO4, filtered and concentrated to an oil. This oil was purified by flash silica chromatography (2 to 5% MeOH/EtOAc) to give an orange oil (0.50 g, 0.52 mmol, 44%, compound 27).

후처리

  1. washthe organic phase washed with saturated NaHCO3
  2. extractionThe aqueous layer was back extracted with EtOAc twice
  3. dry with materialthe combined organic layers dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThis oil was purified by flash silica chromatography (2 to 5% MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-7783565767084e62bb51a84c3a0aea72
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135550B2

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