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Trifluoroacetic acid → (R)-(3-Aminopiperidin-1-yl)(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazol-5-yl)methanone

HRID 2275046
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2275046
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([C:16]2[CH:38]=[C:37]([O:39][CH3:40])[C:19]3[N:20]([CH3:36])[C:21]([C:23]4[N:31]([CH2:32][CH:33]5[CH2:35][CH2:34]5)[C:26]5=[N:27][CH:28]=[CH:29][CH:30]=[C:25]5[CH:24]=4)=[N:22][C:18]=3[CH:17]=2)=[O:15])[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([C:16]2[CH:38]=[C:37]([O:39][CH3:40])[C:19]3[N:20]([CH3:36])[C:21]([C:23]4[N:31]([CH2:32][CH:33]5[CH2:35][CH2:34]5)[C:26]5=[N:27][CH:28]=[CH:29][CH:30]=[C:25]5[CH:24]=4)=[N:22][C:18]=3[CH:17]=2)=[O:15])[CH2:9]1
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Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 118178622(R)-tert-Butyl(1-(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamate

Produkt 1

HCID 73052939(R)-(3-Aminopiperidin-1-yl)(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazol-5-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887Methanol
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-tert-butyl(1-(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamate (1.5587 g, 2.79 mmol) in DCM (10 ml) was added TFA (5 mL, 65.3 mmol) dropwise. The reaction mixture was stirred for 30 minutes and then concentrated under vacuum to afford an oil. The oil was dissolved in methanol and loaded onto a 70 g SCX cartridge. The column was washed with MeOH (2CV) and the product collected as the free base with 2M ammonia in methanol (3CV). The product was concentrated in vacuo yield a crude product. This was purified by high pH MDAP (Method E). Appropriate fractions were combined and concentrated in vacuo to yield the title compound as a white solid, 1.127 g.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. customto afford an oil
  3. washThe column was washed with MeOH (2CV)
  4. customthe product collected as the free base with 2M ammonia in methanol (3CV)
  5. concentrationThe product was concentrated in vacuo
  6. customyield a crude product
  7. customThis was purified by high pH MDAP (Method E)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-37ec4487544742439e83139f93573e9a
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09127003B2

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