Trifluoroacetic acid → (S)-N-((2S,3S)-1-Acetyl-5-((1-(2-cyanophenyl)-1H-indazol-3-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide

HRID 1486064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1486064
[C:1]([N:4]1[C@@H:10]([CH3:11])[C@H:9]([NH:12][C:13](=[O:25])[C@@H:14]([N:16](C)[C:17](=O)OC(C)(C)C)[CH3:15])[C:8](=[O:26])[N:7]([CH2:27][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[C:43]#[N:44])[N:29]=2)[C:6]2[CH:45]=[CH:46][CH:47]=[CH:48][C:5]1=2)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([N:4]1[C@@H:10]([CH3:11])[C@H:9]([NH:12][C:13](=[O:25])[C@@H:14]([NH:16][CH3:17])[CH3:15])[C:8](=[O:26])[N:7]([CH2:27][C:28]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[C:43]#[N:44])[N:29]=2)[C:6]2[CH:45]=[CH:46][CH:47]=[CH:48][C:5]1=2)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 118292660tert-butyl(S)-1-((2S,3S)-1-acetyl-5-((1-(2-cyanophenyl)-1H-indazol-3-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate

Produkt 1

HCID 73425656(S)-N-((2S,3S)-1-Acetyl-5-((1-(2-cyanophenyl)-1H-indazol-3-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a rt solution of tert-butyl(S)-1-((2S,3S)-1-acetyl-5-((1-(2-cyanophenyl)-1H-indazol-3-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (79 mg, 122 μmol) in CH2Cl2 (486 μl) was added TFA (122 μl). The reaction was stirred for 1.5 h, then concentrated and purified by reverse phase preparative HPLC to provide, after extraction from sat. aq. NaHCO3, (S)-N-((2S,3S)-1-acetyl-5-((1-(2-cyanophenyl)-1H-indazol-3-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide (57.0 mg, 85%) as a white solid. MS m/z 550 (MH)+.

Aufarbeitung

  1. concentrationconcentrated
  2. custompurified by reverse phase preparative HPLC
  3. customto provide
  4. extractionafter extraction from sat. aq. NaHCO3, (S)-N-((2S,3S)-1-acetyl-5-((1-(2-cyanophenyl)-1H-indazol-3-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide (57.0 mg, 85%) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-78623dc078f24cf3af90f720f461da0a
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422331B2

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