Triethylamine → tert-butyl 4-((3-ethylphenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methylamino)benzylcarbamate

HRID 2105055Notes

Reaction equation

HRID 2105055 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.Cl[CH:18](C1C=CC=C(CC)C=1)[C:19]1[N:23]([CH3:24])[N:22]=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:20]=1.CCN([CH2:44][CH3:45])CC>C(#N)C>[CH2:15]([C:16]1[CH:2]=[C:3]([N:1]([CH2:18][C:19]2[N:23]([CH3:24])[N:22]=[C:21]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:20]=2)[C:2]2[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[CH:4][CH:3]=2)[CH:4]=[CH:44][CH:45]=1)[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 578039035-(chloro(3-ethylphenyl)methyl)-1-methyl-3-phenyl-1H-1,2,4-triazole

Product 1

HCID 68816261tert-butyl 4-((3-ethylphenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methylamino)benzylcarbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 4-aminobenzylcarbamate (31 mg, 0.14 mmol) was added to a solution of intermediate 370.3 (43 mg,) and Et3N (0.1 mL) in acetonitrile (1 mL) and stirred at 80° C. for 16 h. The mixture was concentrated and purified by flash chromatography (EtOAc/hexanes) to yield 43 mg of intermediate 372.1 as a white solid. LCMS 498.38 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-52e70df9774745a697c36ae6583ebcdb
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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