Acetic Acid → HCID 54767912, compound

HRID 659175Notes

Reaction equation

HRID 659175 reaction equation
[N:1]1[CH:2]=[N:3][N:4]2[CH:9]=[C:8]([C:10]3[N:11]=[C:12]([CH:22]=O)[NH:13][C:14]=3[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=3)[CH:7]=[CH:6][C:5]=12.[NH2:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[CH2:33][N:34]([CH3:36])[CH3:35])[C:28]#[N:29].CC(O)=O.[BH4-].[Na+].Cl>ClCCCl>[N:1]1[CH:2]=[N:3][N:4]2[CH:9]=[C:8]([C:10]3[N:11]=[C:12]([CH2:22][NH:24][C:25]4[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=4[CH2:33][N:34]([CH3:36])[CH3:35])[C:28]#[N:29])[NH:13][C:14]=3[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=3)[CH:7]=[CH:6][C:5]=12

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 66632532HCID 66632532, compoundHCID 86660660HCID 86660660, compound

Product 1

HCID 54767912HCID 54767912, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-((1,2,4)triazolo(1,5-a)pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazole-2-carbaldehyde (0.50 g, 1.64 mmol) in 1,2-dichloroethane (30 mL) were added 3-amino-4-((dimethylamino)methyl)benzonitrile (0.43 g, 2.46 mmol) and AcOH (0.20 g, 3.29 mmol), and the mixture was heated at 80° C. overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in anhydrous MeOH (30 mL). To a methanolic solution at 0° C. was added NaBH4 (0.25 g, 6.57 mmol), and then the mixture was allowed to warm to room temperature and stirred for an additional 3 h. The pH of the reaction mixture was adjusted to 7-8 at 0° C. with 1 N HCl, and then MeOH was removed under reduced pressure. The aqueous mixture was extracted with CH2Cl2 (2×50 mL), and the CH2Cl2 solution was dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of MeOH and CH2Cl2 (1:19 (v/v)) as eluent to give the titled compound (0.60 g, 79%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.99 (s, 1H), 8.36 (s, 1H), 7.86 (dd, 1H, J=9.2, 1.6 Hz), 7.78 (dd, 1H, J=9.2, 0.8 Hz), 7.47 (t, 1H, J=7.6 Hz), 7.23 (br d, 1H, J=7.6 Hz), 7.09 (d, 1H, J=7.6 Hz), 7.01 (d, 1H, J=7.6 Hz), 6.98 (dd, 1H, J=7.6, 1.6 Hz), 6.93 (br s, 1H), 4.59 (s, 2H), 3.63 (s, 2H), 2.53 (s, 3H), 2.33 (s, 6H); MS (ESI) m/z 464.23 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in anhydrous MeOH (30 mL)
  3. temperatureto warm to room temperature
  4. customMeOH was removed under reduced pressure
  5. extractionThe aqueous mixture was extracted with CH2Cl2 (2×50 mL)
  6. dry with materialthe CH2Cl2 solution was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure
  9. customThe residue was purified by MPLC on silica gel using
  10. additiona mixture of MeOH and CH2Cl2 (1:19 (v/v)) as eluent

Sources & evidence

ORD record
ord-03ccf18bb8d94003a74239cd4c03eb89
Source dataset
uspto-grants-2011_12
Patent number
US08080568B1

Reaction notes

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