HCID 817589, compound → HCID 90409239, compound

HRID 2177586Notes

Reaction equation

HRID 2177586 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:9]=[N:8]1>CC(O)=O.[Rh]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:15]2[CH2:14][CH2:13][NH:12][CH2:11][C:10]=2[N:9]=[N:8]1

Participants

4

Reactant 1

HCID 817589HCID 817589, compound

Product 1

HCID 90409239HCID 90409239, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

1-Pyridin-2-yl-1H-[1,2,3]-triazolo[4,5-c]pyridine (23 mg, 0.12 mmol) in HOAc (14 mL) was hydrogenated at 50 bar using Rh/C as catalyst on the H-cube apparatus with a flow rate of 1 ml/min and looped with product recycling for 2 hrs. Reaction was concentrated then partially purified on 12 g SiO2 with 0-10% NH3 MeOH/CH2Cl2. Used without further purification in next reaction. MS (ESI): mass calcd. for C10H11N5, 201.2. m/z found, 202.2 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 8.49 (ddd, J=4.9, 2.0, 0.9 Hz, 1H), 8.18-8.10 (m, 1H), 7.90 (ddd, J=8.3, 7.4, 1.9 Hz, 1H), 7.36-7.27 (m, 1H), 4.12 (t, J=1.4 Hz, 2H), 3.31-3.12 (m, 4H).

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. customthen partially purified on 12 g SiO2 with 0-10% NH3 MeOH/CH2Cl2
  4. customUsed without further purification in next reaction

Sources & evidence

ORD record
ord-fafc5b2b5f6a4966b4ef721775ff12f9
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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