3-(1H-Benzimidazol-2-yl)pyridin-2-amine → HCID 86680261, compound

HRID 921051Notes

Reaction equation

HRID 921051 reaction equation
C([C:5]1[N:10]=[C:9]([NH2:11])[C:8]([C:12]2[NH:24][C:15]3[CH:16]=[N:17][C:18](C(C)(C)C)=[CH:19][C:14]=3[N:13]=2)=[CH:7][N:6]=1)(C)(C)C.N[C:26]1C(C2NC3C=CC=CC=3N=2)=CC=CN=1>>[CH:7]1[C:8]2[C:12]3[N:24]([CH:26]=[N:11][C:9]=2[N:10]=[CH:5][N:6]=1)[C:15]1[C:14](=[CH:19][CH:18]=[N:17][CH:16]=1)[N:13]=3

Participants

3

Reactant 2

HCID 135214193-(1H-Benzimidazol-2-yl)pyridin-2-amineHCID 67996057HCID 67996057, compound

Product 1

HCID 86680261HCID 86680261, compound

Procedure

Preparation analogous to 7), using 32.4 g (100 mmol) of 2-(2-tert-butyl-4-aminopyrimidin-5-yl)-6-tert-butyl-3H-imidazo[4,5-c]pyridine (S56) (employed as equimolar mixture with 2,6-di-tert-butyl-3H-imidazo[4,5-c]-pyridine as obtained from synthesis 27)) instead of 100 mmol of the 2-(2-aminopyridin-3-yl)benzimidazole derivative. After crystallisation from methanol, the crude products are passed through a silica-gel column (heptane:ethyl acetate, 3:1 vv). The solids obtained in this way are freed from low-boiling components and non-volatile secondary components by sublimation (p about 1×10−5 mbar, T about 200-240° C.). Purity according to 1H-NMR typically >99.5%.

Workup

  1. customPreparation analogous to 7),
  2. customAfter crystallisation from methanol
  3. customThe solids obtained in this way
  4. customare freed from low-boiling components and non-volatile secondary components by sublimation (p about 1×10−5 mbar, T about 200-240° C.)

Sources & evidence

ORD record
ord-7ac642b735d2412f8c514840f633bb23
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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