HCID 178486756, compound → HCID 178486754, compound

HRID 1165590Notes

Reaction equation

HRID 1165590 reaction equation
N1C=CN=C1.[CH3:6][CH:7]([O:9][C:10]1[C:11]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29]CC3C=CC=CC=3)=[CH:23][C:12]=2[S:13][C:14]=1[C:15]([NH:17][C:18]1[NH:22][N:21]=[N:20][N:19]=1)=[O:16])[CH3:8]>[Pd].C(O)(=O)C>[CH3:8][CH:7]([O:9][C:10]1[C:11]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([OH:29])=[CH:23][C:12]=2[S:13][C:14]=1[C:15]([NH:17][C:18]1[NH:22][N:21]=[N:20][N:19]=1)=[O:16])[CH3:6]

Participants

4

Reactant 1

HCID 178486756HCID 178486756, compound

Product 1

HCID 178486754HCID 178486754, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

A slurry of 3-(1-methylethoxy)-5-methoxy-6(phenylmethoxy)-N-1H-tetrazol-5-yl-benzo[b]thiophene2-carboxamide imidazole salt (1.55 g, 3 mmoles) and 20% palladium on carbon (0.5 g) in acetic acid (250 mls) is shaken under hydrogen (50 psig) in a Parr apparatus at 40° C. After 19 hours an additional 0.5 g of catalyst and acetic acid (250 mls) are added and shaking continued at 50° C. for 33 hours. The catalyst is filtered from the cooled mixture and rinsed with acetic acid. The filtrate is stripped of solvent under reduced pressure to leave the crystalline product. Recrystallization from methanol gave the pure 3-(1-methylethoxy)-5-methoxy-6-hydroxy-N-lH-tetrazol-5-yl-benzo[b]thiophene-2-carboxamide (0.3 g): mp=245° C. (dec).

Workup

  1. filtrationThe catalyst is filtered from the cooled mixture
  2. washrinsed with acetic acid
  3. customto leave the crystalline product
  4. customRecrystallization from methanol

Sources & evidence

ORD record
ord-d8ec337016b546438e080bbf7c3c2dcc
Source dataset
uspto-grants-1990_03
Patent number
US04910317

Reaction notes

Loading…