Water → HCID 178437446, compound

HRID 1729436Notes

Reaction equation

HRID 1729436 reaction equation
[C:1]([C:3]1[N:8]=[C:7]2[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:31][N:30]=[N:29][N:28]=4)=[CH:17][CH:16]=3)[C:10]([CH2:12][CH3:13])=[N:11][C:6]2=[C:5]([CH3:32])[CH:4]=1)#N.OS(O)(=O)=O.[OH2:38].[NH4+].[OH-:40]>CO>[C:1]([C:3]1[N:8]=[C:7]2[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:28][N:29]=[N:30][N:31]=4)=[CH:17][CH:16]=3)[C:10]([CH2:12][CH3:13])=[N:11][C:6]2=[C:5]([CH3:32])[CH:4]=1)([OH:40])=[O:38]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 178437440HCID 178437440, compound

Product 1

HCID 178437446HCID 178437446, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To neat 5-Cyano-2-ethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine (20 mg) at RT was added H2SO4 (0.5 mL) and water (0.25 mL). The mixture was heated to 100° C. for 3 hours, cooled to 0° C., then made basic by the addition of NH4OH. After adding methanol (5 mL), the mixture was filtered, concentrated, and purified (SiO2, 60:40:1 CH2Cl2 --CH3OH--NH4OH) to give 17 mg of the title compound as a solid. FAB MS (M+ +1)=440; 1H NMR (300 MHz, CD3OD) δ 7.90 (s, 1H), 7.56-7.39 (m, 4H), 7.05 (apparent s, 4H), 5.62 (s, 2H), 2.86 (q, 2H, J=7.5 Hz), 2.67 (s, 3H), 1.26 (t, H, J=7.5 Hz).

Workup

  1. temperaturecooled to 0° C.
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated
  4. custompurified (SiO2, 60:40:1 CH2Cl2 --CH3OH--NH4OH)

Sources & evidence

ORD record
ord-df976a5e9a994f6d8d39345f22c0d7c1
Source dataset
uspto-grants-1994_07
Patent number
US05332744

Reaction notes

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