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 720867ノート

反応式

HRID 720867 の反応式
[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

参加物

7

反応物 4

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

生成物 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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7783565767084e62bb51a84c3a0aea72
出典データセット
uspto-grants-2006_11
特許番号
US07135550B2

反応ノート

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