Hydrochloric Acid → HCID 178509684, compound

HRID 2069953Notes

Reaction equation

HRID 2069953 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=2[O:23]C)[CH:12]=[CH:13][CH:14]=1)(C)(C)C.[N:26]([Sn](CCCC)(CCCC)CCCC)=[N+:27]=[N-:28].C(OCC)(=O)C.Cl>C1(C)C=CC=CC=1>[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[C:16]([OH:23])=[CH:17][CH:18]=[C:19]([C:21]3[NH:22][N:28]=[N:27][N:26]=3)[CH:20]=2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4984872Tributyltin azideHCID 86607705Tert-butyl (5'-cyano-2'-methoxybiphenyl-3-ylmethyl)carbamate

Product 1

HCID 178509684HCID 178509684, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl(5′-cyano-2′-methoxy-biphenyl-3-yl-methyl)-carbamate (0.73 g, 2.16 mmol), prepared as in Reference 19, and azidotributyltin (0.9 mL, 3.2 mmol) was dissolved in toluene (5 mL) and the solution was refluxed for 14 hours. The mixture cooled to room temperature and then workup with ethyl acetate and 1N HCl gave a slurry. The slurry was dried by rotovap and then triturated with hexanes. The solids were collected by filtration and treated with hydrobromic acid (48% aqueous, 15 mL). The mixture was refluxed for 14 hours at 120° C. and then diluted with water (50 mL). The dilution was dried by lyophilization to give 3′-aminomethyl-5-(1H-tetrazol-5-yl)-biphenyl-2-ol (0.4 g).

Workup

  1. temperaturethe solution was refluxed for 14 hours
  2. customgave a slurry
  3. customThe slurry was dried by rotovap
  4. customtriturated with hexanes
  5. filtrationThe solids were collected by filtration
  6. additiontreated with hydrobromic acid (48% aqueous, 15 mL)
  7. temperatureThe mixture was refluxed for 14 hours at 120° C.
  8. additiondiluted with water (50 mL)
  9. customThe dilution was dried by lyophilization

Sources & evidence

ORD record
ord-7012fc8daa304331934a5c0742cda07e
Source dataset
uspto-grants-2012_10
Patent number
US08299110B2

Reaction notes

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