Pyridine → HCID 178474066, compound

HRID 1874838Notes

Reaction equation

HRID 1874838 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[N:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>ClCCl>[C:24]([NH:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[N:8][C:4]=2[CH:3]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178450788HCID 178450788, compound

Product 1

HCID 178474066HCID 178474066, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 1,1-dimethylethyl 5-amino-1H-benzimidazole-2-carboxylate (0.147 g, 0.630 mmol) in dichloromethane (5 mL) was cooled in an ice bath. Pyridine (0.076 mL, 0.945 mmol) and acetic anhydride (0.059 mL, 0.630 mmol) were added. The reaction mixture was filtered and the collected solid was washed with dichloromethane and dried under vacuum to give the title compound (0.160 g, 92%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 13.06 (s, 1H), 10.05 (s, 1H), 8.14 (s, 1H), 7.61 (m, 1H), 7.24 (m, 1H), 2.04 (s, 3H), 1.55 (s, 9H). MS: m/z 276 (M+1).

Workup

  1. temperaturewas cooled in an ice bath
  2. filtrationThe reaction mixture was filtered
  3. washthe collected solid was washed with dichloromethane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-9f944903eee94f01a3e7064d4947e4a0
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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