5-n-Butyl-2-cyanomethyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one → HCID 178441933, compound

HRID 36214Notes

Reaction equation

HRID 36214 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:7](=[O:13])[N:8]([CH2:10][C:11]#[N:12])[N:9]=1)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:7](=[O:13])[N:8]([CH2:10][C:11]#[N:12])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 199394385-n-Butyl-2-cyanomethyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 178441933HCID 178441933, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Deprotection of 5-n-butyl-2-cyanomethyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one in 67% aqueous acetic acid was accomplished by the procedure of Example 3, Step B. After work-up, the residue was flash chromatographed over silica gel (15 mL for 0.082 mmole, gradient elution using 3-10% MeOH/CH2Cl2) to give a 32% yield of the desired material as a glassy solid, mp 86°-88° C., homogeneous by TLC in 10% MeOH/CH2Cl2, mass spectrum (FAB) m/e 415 (M+1)+.

Workup

  1. customchromatographed over silica gel (15 mL for 0.082 mmole, gradient elution using 3-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b02cab541b51428dbdc61dd43c6bd0a1
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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