Acetic Acid → HCID 178513791, compound

HRID 912715Notes

Reaction equation

HRID 912715 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[CH:3][CH:2]=1.N[C:14]1[NH:18][CH:17]=[N:16][C:15]=1[C:19]([NH2:21])=[O:20].C(O)(=O)C.C([BH3-])#[N:27].[Na+]>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH:27][C:15]2([C:19]([NH2:21])=[O:20])[CH2:14][NH:18][CH:17]=[N:16]2)=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 96795-Aminoimidazole-4-carboxamideHCID 780724-QuinolinecarboxaldehydeHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 178513791HCID 178513791, compound

Procedure

The title compound was prepared in accordance with the general method described in Example 17(e) using quinoline-4-carbaldehyde (1.0 g, 6.4 mmol), 5-aminoimidazole-4-carboxamide (0.80 g, 6.4 mmol), acetic acid (0.44 mL, 7.6 mmol) and sodium cyanoborohydride (0.48 g, 7.6 mmol) with the exception that after stirring o.n., another portion of sodium cyanoborohydride (0.48 g, 7.6 mmol) was added and the mixture heated to reflux for 4 h. After cooling to r.t., the solution was concentrated in vacuo. A portion of the 2.9 g of crude material obtained was used in the next step without further purification. MS (ESI) m/z 268 (M+1).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 h
  3. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-d3ec3dce0068405aa7b53bd75f44e39e
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

Loading…