5-Aminopyridine-2-carbonitrile → HCID 67390012, compound

HRID 913283Notes

Reaction equation

HRID 913283 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10](Cl)[N:9]=2)[N:5]=[CH:4][N:3]=1.[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=1.[CH3:24][O:25][CH2:26][C@@H:27]([NH2:29])[CH3:28]>O1CCCC1>[CH3:24][O:25][CH2:26][C@@H:27]([NH:29][C:10]1[N:9]=[C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=3)[N:7]=2)[CH:13]=[CH:12][N:11]=1)[CH3:28]

Participants

5

Reactant 3

HCID 38713955-Aminopyridine-2-carbonitrileHCID 70215362-Propanamine, 1-methoxy-, (2S)-HCID 86646773HCID 86646773, compound2×

Product 1

HCID 67390012HCID 67390012, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-chloro-4-(2-chloro-4-pyrimidinyl)-1,3,5-triazine (i.e., the product of Example 1, Step B) (100 mg, 0.43 mmol) in tetrahydrofuran (2.0 mL) was added 5-amino-2-pyridinecarbonitrile (86 mg, 0.72 mmol), and the resulting mixture was stirred at 40° C. for 3 h. To this mixture was added (S)-1-methoxy-2-propylamine (0.2 mL), and the resulting mixture was refluxed for 2 h. The solution was concentrated and purified using column chromatography on silica gel eluted with a gradient of 70% to 80% ethyl acetate in hexanes to give 84 mg of the title compound as a yellow solid.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. concentrationThe solution was concentrated
  3. custompurified
  4. washeluted with a gradient of 70% to 80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-aa7ac8d227f345faa9e9716a42e2683e
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

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