Diisopropylethylamine → tert-butyl (2S)-2-{[4-(methylamino)phenyl]carbonylamino}-4-{N-[2-(2-{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]ethoxy}ethoxy)ethyl]carbamoyl}butanoa te

HRID 720868노트

반응식

HRID 720868 반응식
[N:1]1([NH:7][C:8]([NH:10][C:11]2[C:16]3[C:17](=[O:34])[C:18]4[C:19](=[N:20][NH:21][C:22]=4[C:23]4[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29]([OH:31])=O)=[CH:25][CH:24]=4)[C:15]=3[CH:14]=[CH:13][CH:12]=2)=[O:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][NH:53][C:54]([CH2:56][CH2:57][C@H:58]([NH:66][C:67]([C:69]1[CH:74]=[CH:73][C:72]([NH:75][CH3:76])=[CH:71][CH:70]=1)=[O:68])[C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])=[O:55].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>[CH3:76][NH:75][C:72]1[CH:73]=[CH:74][C:69]([C:67]([NH:66][C@@H:58]([CH2:57][CH2:56][C:54](=[O:55])[NH:53][CH2:52][CH2:51][O:50][CH2:49][CH2:48][O:47][CH2:46][CH2:45][O:44][CH2:43][CH2:42][O:41][CH2:40][CH2:39][O:38][CH2:37][CH2:36][NH:35][C:29](=[O:31])[CH2:28][O:27][C:26]2[CH:32]=[CH:33][C:23]([C:22]3[NH:21][N:20]=[C:19]4[C:15]5[CH:14]=[CH:13][CH:12]=[C:11]([NH:10][C:8](=[O:9])[NH:7][N:1]6[CH2:6][CH2:5][O:4][CH2:3][CH2:2]6)[C:16]=5[C:17](=[O:34])[C:18]=34)=[CH:24][CH:25]=2)[C:59]([O:61][C:62]([CH3:65])([CH3:63])[CH3:64])=[O:60])=[O:68])=[CH:70][CH:71]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66933864HCID 66933864, 화합물HCID 1785259502-(4-(5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-3-yl}phenoxy)acetic Acid

생성물 1

HCID 178482177tert-butyl (2S)-2-{[4-(methylamino)phenyl]carbonylamino}-4-{N-[2-(2-{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]ethoxy}ethoxy)ethyl]carbamoyl}butanoa te

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Compound 25 (0.60 g, 1 mmol) and compound 26 (0.46 g, 1 mmol) were dissolved in 10 ml DMF and HBTU (0.7 g, 1.8 mmol) was added as a solid followed by DIEA (1.0 ml, 5.7 mmol). The reaction mixture was stirred at room temperature overnight, diluted with EtOAc and the organic phase washed with 0.5N NaOH, brine, dried over MgSO4, filtered and concentrated to an oil. This oil was purified by flash silica chromatography (10 to 20% MeOH/EtOAc) to give a yellow foam (0.65 g, 0.62 mmol, 62%, compound 28).

후처리

  1. washthe organic phase washed with 0.5N NaOH, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. customThis oil was purified by flash silica chromatography (10 to 20% MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-e02df997e5cc496a85184447edf42f8d
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135550B2

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