Hydrochloric Acid → HCID 178509684, compound

HRID 1752905Notes

Reaction equation

HRID 1752905 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:24]C)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16]C(=O)OC(C)(C)C)[CH:10]=2)[CH:8]=1)#[N:2].[N:26]([Sn](CCCC)(CCCC)CCCC)=[N+:27]=[N-:28].C(OCC)(=O)C.Cl>C1(C)C=CC=CC=1>[NH2:16][CH2:15][C:11]1[CH:10]=[C:9]([C:7]2[C:6]([OH:24])=[CH:5][CH:4]=[C:3]([C:1]3[NH:2][N:28]=[N:27][N:26]=3)[CH:8]=2)[CH:14]=[CH:13][CH:12]=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-7443ca64c7b64aefb32b09caba809a9c
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

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