Diisopropylethylamine → HCID 69675210, Verbindung

HRID 1751541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1751541
[CH3:1][CH:2]([CH3:51])[C@H:3]([NH:46][C:47](=[O:50])[O:48][CH3:49])[C:4](=[O:45])[N:5]1[C@H:13]([C:14]2[NH:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[C:30]([C:35]6[NH:39][C:38]([C@@H:40]7[CH2:44][CH2:43][CH2:42][NH:41]7)=[N:37][CH:36]=6)[CH:31]=5)[CH:26]=4)=[CH:21][CH:20]=3)=[CH:17][N:18]=2)[CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6]1.[CH3:52][O:53][C:54]([NH:56][C@H:57]([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[C:58](O)=[O:59])=[O:55].CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CCOC(C)=O.CN(C)C=O>[CH3:49][O:48][C:47](=[O:50])[NH:46][C@@H:3]([CH:2]([CH3:51])[CH3:1])[C:4]([N:5]1[C@H:13]([C:14]2[NH:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[C:30]([C:35]6[NH:39][C:38]([C@@H:40]7[CH2:44][CH2:43][CH2:42][N:41]7[C:58](=[O:59])[C@H:57]([NH:56][C:54]([O:53][CH3:52])=[O:55])[C:61]7[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=7)=[N:37][CH:36]=6)[CH:31]=5)[CH:26]=4)=[CH:21][CH:20]=3)=[CH:17][N:18]=2)[CH2:12][C:7]2([O:8][CH2:9][CH2:10][O:11]2)[CH2:6]1)=[O:45]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acidHCID 67681804Methyl (S)-3-methyl-1-oxo-1-((S)-8-(5-(4-(6-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)butan-2-ylcarbamateHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate

Produkt 1

HCID 69675210HCID 69675210, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl (S)-3-methyl-1-oxo-1-((S)-8-(5-(4-(6-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)butan-2-ylcarbamate as 3HCl salt (200 mg, 0.24 mmol), (R)-2-(methoxycarbonylamino)-2-phenylacetic acid (60 mg, 0.288 mmol), and COMU (154 mg, 0.36 mmol) were all weighed out in a scintillation vial and anhydrous N,N-dimethylformamide (2.4 mL) was added and without stirring to this mixture was then added DIPEA (124 mg, 0.96 mmol) and the mixture was sonicated to dissolve all the reactants as quickly as possible. The mixture was then stirred for 2 h at room temperature. The crude mixture was diluted with EtOAc and washed with brine, 10% Na2CO3, brine and the organic layer was dried over MgSO4. The filtrate was concentrated down and the residue was purified by normal phase column chromatography (5% MeOH/DCM). MS (ESI) m/z 881.84 [M+H]+. (95 mg, 45%).

Aufarbeitung

  1. additionwas added
  2. dissolutionto dissolve all the reactants as quickly as possible
  3. stirringThe mixture was then stirred for 2 h at room temperature
  4. washwashed with brine, 10% Na2CO3, brine
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationThe filtrate was concentrated down
  7. customthe residue was purified by normal phase column chromatography (5% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-846b77b9997944c2bd60321922e6e723
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156823B2

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