Acetic Acid → HCID 117803008, compound

HRID 520326Notes

Reaction equation

HRID 520326 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[C:14]1[C:19]([CH2:20][O:21][Si](C(C)(C)C)(C)C)=[C:18]([Cl:29])[CH:17]=[CH:16][N:15]=1.[C:31](O)(=[O:33])[CH3:32]>>[C:31]([O:21][CH2:20][C:19]1[C:14]([C:13]2[NH:1][C:2]3[CH:7]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=3[N:12]=2)=[N:15][CH:16]=[CH:17][C:18]=1[Cl:29])(=[O:33])[CH3:32]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 131735497HCID 131735497, compound

Product 1

HCID 117803008HCID 117803008, compoundYield 44%

Procedure

A solution of 160g (10 g, 22 mmol) in acetic acid (100 mL) was stirred at 120° C. for 5 h. See FIG. 5. The mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluting with petroleum ether:ethyl acetate=3:1) to afford (2-(6-(tert-butyl)-1H-benzo[d]imidazol-2-yl)-4-chloropyridin-3-yl)methyl acetate 160h (3.5 g, 44%) as a yellow solid. MS-ESI: [M+H]+ 358.2.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluting with petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-dc15a0889c534e5e96a32f921db6ff82
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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