Trifluoroacetic acid → 2-((1R,6S)-3,8-Diazabicyclo[4.2.0]octan-8-yl)-N,N-dimethylpyridin-4-amine

HRID 1193097Notes

Reaction equation

HRID 1193097 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15]3)[CH2:10]2)[CH:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C@@H:16]12[N:9]([C:5]3[CH:4]=[C:3]([N:2]([CH3:24])[CH3:1])[CH:8]=[CH:7][N:6]=3)[CH2:10][C@@H:11]1[CH2:12][CH2:13][NH:14][CH2:15]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67117087(1R,6S)-tert-butyl 8-(4-(dimethylamino)pyridin-2-yl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate

Product 1

HCID 671172692-((1R,6S)-3,8-Diazabicyclo[4.2.0]octan-8-yl)-N,N-dimethylpyridin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1R,6S)-tert-butyl 8-(4-(dimethylamino)pyridin-2-yl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate (150 mg, 0.45 mmol) in DCM (5 mL) was added TFA (2 mL). The resulting mixture was allowed to stir at ambient temperature. After 16 hours the crude mixture was concentrated under reduced pressure. The resulting trifluoroacetic acid salt of the title compound was used without further purification. MS (ESI) mass calcd. for C13H20N4, 232.2; m/z found, 233.2 [M+H]+.

Workup

  1. concentrationAfter 16 hours the crude mixture was concentrated under reduced pressure
  2. customThe resulting trifluoroacetic acid salt of the title compound was used without further purification

Sources & evidence

ORD record
ord-effc48eb6ed54ecb8c3d1e6989810e11
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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