Hydrochloric Acid → Telmisartan

HRID 1960058Notes

Reaction equation

HRID 1960058 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:17]([CH:22]=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[C:7]2[CH:24]=[C:25](C3N=CN(C)C=3)[CH:26]=[C:27]([CH3:28])[C:6]=2[N:5]=1)[CH2:2][CH3:3].Cl.[OH2:36]>C(#N)C.OO>[CH3:3][CH2:2][CH2:1][C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([OH:23])=[O:36])=[CH:14][CH:15]=2)[C:7]2[CH:24]=[C:25]([C:4]3[N:8]([CH3:9])[C:7]4[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=4[N:5]=3)[CH:26]=[C:27]([CH3:28])[C:6]=2[N:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962Water3×HCID 11947986HCID 11947986, compound

Product 1

HCID 65999Telmisartan

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 156 mg of NaClO2.4H2O in 1 mL of water was added dropwise by canilla to a stirred mixture of 4′-[(2-n-propyl-4-methyl-6-(1-methyl-imidazol-4-yl)-benzimidazol-1-yl)methyl]-biphenyl-2-carboxaldehyde (230 mg) in 1 mL of acetonitrile, 0.16 ml of 10 solution of NaH2PO4 in water and 0.23 mL of 30% H2O2 at the temperature 10° C. pH of the mixture was adjusted to 2 with concentrated hydrochloric acid. Stirring was continued for 1.5 h at room temperature. Reaction mixture was poured in 1.2 mL of water, stirred for 15 minutes, product filtered, washed with water and dried in vacuo to yield 210 mg of telmisartan.

Workup

  1. customReaction mixture
  2. stirringstirred for 15 minutes
  3. filtrationproduct filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-15b253e78f55431f870d19518c4a9b46
Source dataset
uspto-grants-2013_04
Patent number
US08410285B2

Reaction notes

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