Acetic Acid → HCID 90408896, compound

HRID 2177609Notes

Reaction equation

HRID 2177609 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:3]=1.C(O)(=O)C.[N:20](OC(C)(C)C)=O>C1COCC1>[CH3:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[N:20][N:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 90408825HCID 90408825, compound

Product 1

HCID 90408896HCID 90408896, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methyl-N4-(pyridin-2-yl)pyridine-3,4-diamine (550 mg, 2.7 mmol) in THF (30 mL) was added acetic acid (0.17 mL, 6.49 mmol) and tert-butyl nitrite (0.54 mL, 4.12 mmol). The reaction was then heated to reflux and stirred overnight. The reaction was concentrated and the residue was purified by chromatography on silica gel (0-10% [2M NH3 in MeOH]CH2Cl2) to give the desired product as a yellow gum (408 mg, 70%). MS (ESI) mass calcd. C11H9N5, 211.09. m/z found, 212.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 9.44 (d, J=0.9, 1H), 8.67-8.62 (m, 1H), 8.37 (s, 1H), 8.31-8.23 m, 1H), 8.01-7.96 (m, 1H), 7.41-7.35 (m, 1H), 2.80 (s, 3H).

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. concentrationThe reaction was concentrated
  4. customthe residue was purified by chromatography on silica gel (0-10% [2M NH3 in MeOH]CH2Cl2)

Sources & evidence

ORD record
ord-df1684ba90f74e1aabcb7efd297bd4dd
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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