Pyruvic Acid → HCID 22380146, compound

HRID 895571Notes

Reaction equation

HRID 895571 reaction equation
[CH2:1]([N:4]1[C:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:7]=2[N:6]=[C:5]1[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19]1[N:24]=[C:23]([F:25])[CH:22]=[CH:21][CH:20]=1)[CH2:2][CH3:3].[C:26](O)(=O)[C:27](C)=[O:28].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>[N+]([O-])([O-])=O.[Ag+].C(Cl)Cl.O>[F:25][C:23]1[N:24]=[C:19]([C:15]2[N:14]([CH2:13][C:5]3[N:4]([CH2:1][CH2:2][CH3:3])[C:8]4[CH:9]=[CH:10][N:11]=[C:12]([C:27](=[O:28])[CH3:26])[C:7]=4[N:6]=3)[CH:18]=[CH:17][N:16]=2)[CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 1060Pyruvic AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22380117HCID 22380117, compound

Product 1

HCID 22380146HCID 22380146, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To the mixture of H2O (5 mL) and CH2Cl2 (5 mL) is added 1-Propyl-2-{[2-(2-fluoropyrid-6-yl)-1H-imidazol-1-yl]methyl}-5-aza-1H-benzimidazole (168 mg, 0.5 mmol), pyruvic acid (132 mg, 1.5 mmol), silver nitrate (7 mg, 0.04 mmol), (NH4)2S2O8 (342 mg, 1.5 mmol), and sulfuric acid (98%, 100 mg, 1.0 mmol). The mixture is heated to 40° C. for 2 hr, then cooled to room temperature. The aqueous solution is neutralized to pH 8 with saturated sodium bicarbonate solution and extracted with CH2Cl2. The combined organic layers are dried over Na2SO4 and solvent is removed to give a brown solid. Purification by preparative TLC provides ′1-(2-{[2-(6-fluoropyridin-2-yl)-1H-imidazol-1-yl]methyl}-1-propyl-1H-imidazo[4,5-c]pyridin-4-yl)ethanone as white solid. 1H NMR (CDCl3) δ 8.48 (d, 1H), 8.12 (dd, 1H), 7.88 (q, 1H), 7.44 (d, 1H), 7.23 (d, 1H), 7.11 (d, 1H), 6.88 (dd, 1H), 6.40 (s, 2H), 4.22 (q, 2H), 2.84 (s, 3H), 1.58 (m, 2H), 0.74 (t, 3H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layers are dried over Na2SO4 and solvent
  4. customis removed
  5. customto give a brown solid
  6. customPurification by preparative TLC

Sources & evidence

ORD record
ord-ac8d6a2c23d24ddcb1616d5a42bdaff4
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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