Reaction #160986

ord-3f7848b287eb4132b22aef5990c95ddc

Reaction equation

O=C(Nc1ccc(SC(F)(F)F)nc1)c1cnc(Cl)c(Br)c1
5-bromo-6-chloro-N-(6-((trifluoromethyl)thio)pyridin-3-yl)nicotinamide
O[C@@H]1CCNC1
(R)-pyrrolidin-3-ol
→
O=C(Nc1ccc(SC(F)(F)F)nc1)c1cnc(N2CC[C@@H](O)C2)c(Br)c1
title compound
O=C(Nc1ccc(SC(F)(F)F)nc1)c1cnc(N2CC[C@@H](O)C2)c(Br)c1
(R)-5-Bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(6-((trifluoromethyl)thio)pyridin-3-yl)nicotinamide

Reactants

O=C(Nc1ccc(SC(F)(F)F)nc1)c1cnc(Cl)c(Br)c1
5-bromo-6-chloro-N-(6-((trifluoromethyl)thio)pyridin-3-yl)nicotinamide
O[C@@H]1CCNC1
(R)-pyrrolidin-3-ol

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto afford an off-white powder

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 8.1 using 5-bromo-6-chloro-N-(6-((trifluoromethyl)thio)pyridin-3-yl)nicotinamide (Stage 32.2) and (R)-pyrrolidin-3-ol to afford an off-white powder. HPLC (Condition 4) tR=5.53 min, UPLC-MS (Condition 3) tR=1.01 min, m/z=463.1 [M+H]+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08829195B2uspto-grants-2014_09