3-Mercaptopropionic Acid → HCID 23303066, compound

HRID 1489007Notes

Reaction equation

HRID 1489007 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([C:10](=[O:23])[C:11]2[N:18]3[C:14](=[N:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=43)[S:13][N:12]=2)[C:4]=1[CH3:24].S[CH2:26]CC(O)=O.[C:31](=[O:34])(O)[O-:32].[Na+]>CO.Cl>[NH:12]=[C:11]([N:18]1[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]=[C:14]1[SH:13])[C:10]([C:5]1[C:4]([CH3:24])=[C:3]([O:2][CH3:1])[C:8]([CH3:9])=[CH:7][N:6]=1)=[O:23].[SH:13][C:14]1[NH:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([C:10](=[O:23])[C:31]([O:32][CH3:26])=[O:34])[C:4]=1[CH3:24]

Participants

8

Reactant 3

HCID 65143-Mercaptopropionic AcidHCID 516892Sodium BicarbonateHCID 9819222HCID 9819222, compound

Product 3

HCID 23303066HCID 23303066, compoundHCID 178492284HCID 178492284, compoundHCID 178527775HCID 178527775, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a suspension of 250 mg of 3-[(4-methoxy-3,5-dimethyl-2-pyridyl)oxomethyl]-1,2,4-thiadiazolo[4,5-a]benzimidazole in 125 mL methanol and 38 mL 0.1M hydrochloric acid was added 161 μL of 3-mercaptopropionic acid. After complete degradation of the starting material, the mixture was neutralized to pH 6 with aqueous sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate was dried on anhydrous magnesium sulfate and evaporated. The crude material was purified by chromatography to give 93 mg of 2-imino-2-(2-mercapto-1-benzimidazolyl)-1-(4-methoxy-3,5-dimethyl-2-pyridyl) ethanone, 65 mg of 2-mercaptobenzimidazole and 61 mg of methyl 2-(4-methoxy-3,5-dimethyl-2-pyridyl)-2-oxoacetate. 2-Imino-2-(2-mercapto-1-benzimidazolyl)-1-(4-methoxy-3,5-dimethyl-2-pyridyl)ethanone: 1H NMR (CDCl3) δ10.55 (br s, 1H, NH or SH), 10.35 (br s, 1H, NH or SH), 8.10 (d, 1H, J=7 Hz, ArH), 7.80 (s, 1H, H6 of pyridyl), 7.35-7.20 (m, 2H, 2×ArH), 7.10 (d, 1H, J=7.9 Hz, ArH), 3.75 (s, 3H, OCH3), 2.60 (s, 3H, ARCH3), 2.15 (s, 3H, ArCH3) ppm; IR (KBr) ν3262, 1691, 1635, 1502, 1458, 1396, 1328, 1272, 1247, 1004, 746 cm-1 ; MS (electrospray)m/z 341 (MH+), 191 (MH+ -2-mercaptobenzimidazole). 2-Mercaptobenzimidazole: the material was found to be identical to an authentic sample purchased from Aldrich Chemical Co. by 1H NMR, IR and TLC. Methyl 2-(4-methoxy-3,5-dimethyl-2-pyridyl)-2-oxoacetate: 1H NMR (CDCl3) δ8.45 (s, 1H, ArH), 4.1 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 2.65 (s, 3H, ArCH3), 2.4 (s, 3H, ArCH3) ppm; IR (KBr) ν1747, 1703, 1468, 1394, 1310, 1242, 1206, 1120, 1004, 740 cm-1 ; MS m/z 224 (M+ +H), 164 (M+ -CO2Me), 136 (M+ -CO2Me-CO).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate was dried on anhydrous magnesium sulfate
  3. customevaporated
  4. customThe crude material was purified by chromatography

Sources & evidence

ORD record
ord-7c153e7c361b400ba9111d6defbdfe0d
Source dataset
uspto-grants-1997_10
Patent number
US05677302

Reaction notes

Loading…