3-(1H-Benzimidazol-2-yl)pyridin-2-amine → HCID 86680260, compound

HRID 921050Notes

Reaction equation

HRID 921050 reaction equation
C([C:5]1[N:10]=[C:9]([NH2:11])[C:8]([C:12]2[NH:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:7][N:6]=1)(C)(C)C.N[C:22]1C(C2NC3C=CC=CC=3N=2)=CC=CN=1>>[CH:7]1[C:8]2[C:12]3[N:16]([CH:22]=[N:11][C:9]=2[N:10]=[CH:5][N:6]=1)[C:15]1[C:14](=[CH:20][CH:19]=[CH:18][CH:17]=1)[N:13]=3

Participants

3

Reactant 2

HCID 135214193-(1H-Benzimidazol-2-yl)pyridin-2-amineHCID 67995423HCID 67995423, compound

Product 1

HCID 86680260HCID 86680260, compound

Procedure

Preparation analogous to 7), using 26.7 g (100 mmol) of 2-(2-tert-butyl-4-aminopyrimidin-5-yl)benzimidazole (S55) (employed as equimolar mixture with 2-tert-butylbenzimidazole as obtained from synthesis 26)) 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-f8e50adf4fa64461b726ec31d1b2844a
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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