Reaktion #712106

ord-2c55ca560fcf4a79b52e433414cbe81d

Reaktionsgleichung

O=C(O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1
6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid
C1S[C@@H]2CN[C@H]1C2.Cl
(1S,4S)-2-thia-5-azabicyclo[2.2.1]heptane hydrochloride
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CCN(C(C)C)C(C)C
DIEA
→
O=C(c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1)N1C[C@@H]2C[C@H]1CS2
title compound
O=C(c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1)N1C[C@@H]2C[C@H]1CS2
[6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridin-2-yl]-(1S,4S)-2-thia-5-aza-bicyclo[2.2.1]hept-5-yl-methanone

Edukte

O=C(O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1
6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid
C1S[C@@H]2CN[C@H]1C2.Cl
(1S,4S)-2-thia-5-azabicyclo[2.2.1]heptane hydrochloride
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CCN(C(C)C)C(C)C
DIEA

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

In analogy to the procedure described in Example 47 b), 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (Example 1 b)) was reacted with (1S,4S)-2-thia-5-azabicyclo[2.2.1]heptane hydrochloride (125136-43-8) in the presence of TBTU and DIEA to obtain the title compound as colorless oil; MS (EI): m/e=382.5 [MH+].

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09303012B2uspto-grants-2016_04