HCID 67464385, compound → HCID 67462435, compound

HRID 2202799Notes

Reaction equation

HRID 2202799 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[Cl:23])([OH:16])[CH2:12]2)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:23][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:17]=1[C:11]1([OH:16])[CH2:12][CH:13]2[NH:8][CH:9]([CH2:15][CH2:14]2)[CH2:10]1

Participants

4

Reactant 1

HCID 67464385HCID 67464385, compound

Product 1

HCID 67462435HCID 67462435, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3-(3-Chloro-pyridin-4-yl)-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.34 g, 1.0 mmol) was dissolved in TFA (1 mL) and DCM (2 mL). The mixture was stirred for 1 hour and the solvent removed by evaporation under vacuum and the residues were passed through an SCX cartridge, eluting with 2 M ammonia in methanol to give the title compound (0.24 g, 1.0 mmol). 1H NMR (400 MHz, CDCl3): δ 8.49 (s, 1H), 8.46 (d, 1H), 7.66 (d, 1H), 3.74 (m, broad, 2H), 2.79-2.71 (m, broad, 2H), 2.25-2.17 (m, broad, 3H), 1.98-1.85 (m, broad, 3H), 1.70-1.62 (m, broad, 2H).

Workup

  1. customthe solvent removed by evaporation under vacuum
  2. washeluting with 2 M ammonia in methanol

Sources & evidence

ORD record
ord-e070e924fab84c889350ce54b793ca1c
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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