Hydrochloric Acid → HCID 78320465, compound

HRID 2206446Notes

Reaction equation

HRID 2206446 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[CH2:10]=O.[ClH:12].[CH2:13]([N:15]([CH2:30][CH3:31])[C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=O)=[CH:18][CH:17]=1)[CH3:14]>C(O)C>[Cl-:12].[CH2:13]([N:15]([CH2:30][CH3:31])[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:7]([C:6]3[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:10]=[N+:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=23)=[CH:18][CH:17]=1)[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7732P-AnisidineHCID 86732005HCID 86732005, compound

Product 1

HCID 78320465HCID 78320465, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

was prepared according to general procedure (A), in which 28 μg 4-methoxyaniline (0.22 mmol, 1 equiv), 24 μl formalin (0.34 mmol, 1.5 equiv), 0.14 mL 3.14 M hydrochloric acid in ethanol (0.45 mmol, 2 equiv) and 57 mg (4-(diethylamino)phenyl)(pyridin-2-yl)methanone (0.22 mmol, 1 equiv) were combined in 0.45 mL ethanol and maintained at room temperature for 12 hours. The reaction was concentrated in vacuo and dried under high vacuum at 0.2 Torr. The crude material was triturated with 1.5 mL acetone, which resulted in the formation of a solid. The suspension was then filtered and rinsed with (2:1) acetone/diethylether three times using 1 mL of (2:1) acetone/diethylether for each rinse. The resulting solid was dried under high vacuum at 0.2 Torr for 48 hours to provide 80 mg 1-(4-(diethylamino)phenyl)-2-(4-methoxyphenyl)-2H-imidazo[1,5-a]pyridin-4-ium chloride (0.18 mmol, a 80% yield) as a cream colored solid. This material was determined to be the monocationic salt by titration with sodium hydroxide.

Workup

  1. customwas prepared
  2. concentrationThe reaction was concentrated in vacuo
  3. customdried under high vacuum at 0.2 Torr
  4. customThe crude material was triturated with 1.5 mL acetone, which
  5. customresulted in the formation of a solid
  6. filtrationThe suspension was then filtered
  7. washrinsed with (2:1) acetone/diethylether three times
  8. customThe resulting solid was dried under high vacuum at 0.2 Torr for 48 hours

Sources & evidence

ORD record
ord-fd4d9df7d115485bbb13e2b862fb61b5
Source dataset
uspto-grants-2016_06
Patent number
US09371448B2

Reaction notes

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