Hydrochloric Acid → HCID 178502157, Verbindung

HRID 2392434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2392434
[CH3:1][O:2][C:3](=[O:48])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][CH:18]=[C:19]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:31]4[CH:36]=[CH:35][C:34]([C:37](=[O:47])[CH2:38][NH:39][C:40](OC(C)(C)C)=[O:41])=[CH:33][CH:32]=4)[CH:27]=3)[CH:22]=2)[N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].Cl.CCN(C(C)C)C(C)C.[C:59]([O:63][C:64]([N:66]1[CH2:70][CH:69]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:68][CH:67]1C(O)=O)=[O:65])([CH3:62])([CH3:61])[CH3:60].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O1CCOCC1.CN(C=O)C.CCOC(C)=O>[C:59]([O:63][C:64]([N:66]1[CH2:70][CH:69]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:68][CH:67]1[C:40](=[O:41])[NH:39][CH2:38][C:37]([C:34]1[CH:35]=[CH:36][C:31]([C:26]2[CH:25]=[CH:24][C:23]3[C:28](=[CH:29][CH:30]=[C:21]([C:19]4[N:20]=[C:16]([CH:12]5[CH2:13][CH2:14][CH2:15][N:11]5[C:9](=[O:10])[CH:5]([NH:4][C:3]([O:2][CH3:1])=[O:48])[CH:6]([CH3:8])[CH3:7])[NH:17][CH:18]=4)[CH:22]=3)[CH:27]=2)=[CH:32][CH:33]=1)=[O:47])=[O:65])([CH3:61])([CH3:62])[CH3:60]

Komponenten

10

Edukt 5

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2×HCID 47125061-(1,1-Dimethylethyl) 4-phenyl-1,2-pyrrolidinedicarboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178502158{1-[2-(4-{6-[4-(2-Tert-butoxycarbonylamino-acetyl)-phenyl]-naphthalen-2-yl}-1h-imidazol-2-yl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester

Produkt 1

HCID 178502157HCID 178502157, VerbindungAusbeute 174,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

{1-[2-(4-{6-[4-(2-tert-Butoxycarbonylamino-acetyl)-phenyl]-naphthalen-2-yl]-1H-imidazol-2-yl)-pyrrolidine-1-carbonyl]-2-methyl-propyl]-carbamic acid methyl ester (61.0 mg, 0.095 mmol) was dissolved in DCM (1 mL) and HCl in dioxane (4M, 1 mL) was added and stirring at room temperature was continued. After 90 minutes, all volatiles were removed in vacuo. The crude material was used in the next step without further purification. The crude material was dissolved in DMF (1.0 mL) and DIEA (23.7 mg, 0.183 mmol) was added. A solution of 4-Phenyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (17.8 mg, 0.061 mmol), HATU (23.3 mg, 0.061 mmol) and DIEA (7.9 mg, 0.061 mmol) in DMF (0.5 mL) was added. The reaction was stirred at room temperature. After 20 minutes, the reaction was diluted with EtOAc and was washed with brine, saturated sodium bicarbonate solution, brine, and was dried over sodium sulfate. Filtration and removal of solvents in vacuo gave the crude material (88 mg), which was used in the next step without further purification.

Aufarbeitung

  1. customall volatiles were removed in vacuo
  2. customThe crude material was used in the next step without further purification
  3. dissolutionThe crude material was dissolved in DMF (1.0 mL)
  4. stirringThe reaction was stirred at room temperature
  5. waitAfter 20 minutes
  6. washwas washed with brine, saturated sodium bicarbonate solution, brine
  7. dry with materialwas dried over sodium sulfate
  8. filtrationFiltration and removal of solvents in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4446ccf85505499ab9c170f6b10c74d6
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273341B2

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