Triethylamine → HCID 178449569, compound

HRID 1622134Notes

Reaction equation

HRID 1622134 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([OH:20])=[CH:11][CH:12]=[C:13]([C:15]3[NH:19][N:18]=[N:17][N:16]=3)[CH:14]=2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[C:28]([N:32]=[C:33]=[O:34])([CH3:31])([CH3:30])[CH3:29].C(OCC)(=O)C>CN(C)C=O.O>[C:28]([NH:32][C:33]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([C:15]3[NH:19][N:18]=[N:17][N:16]=3)[CH:12]=[CH:11][C:10]=2[OH:20])[CH:6]=[CH:7][CH:8]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 62412tert-Butyl isocyanateHCID 178509684HCID 178509684, compound

Product 1

HCID 178449569HCID 178449569, compoundYield 131.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3′-aminomethyl-5-(1H-tetrazol-5-yl)-biphenyl-2-ol (0.31 g, 1.16 mmol) was dissolved in dimethylformamide (10 mL) and the solution was treated with triethylamine (0.8 mL, 5.8 mmol) and tert-butylisocyanate (0.14 mL, 1.27 mmol). The mixture was stirred at room temperature for 2 hours. Workup with ethyl acetate and water, followed by drying afforded 0.56 g (quant.) of the crude 1-tert-butyl-3-[2′-hydroxy-5′-(1H-tetrazol-5-yl)-biphenyl-3-ylmethyl]-urea.

Workup

  1. customby drying

Sources & evidence

ORD record
ord-018e1e099a7640cab881336bcf3ad8c7
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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