HCID 21358716, compound → HCID 21358705, compound

HRID 1167827Notes

Reaction equation

HRID 1167827 reaction equation
[C:1]([O:5][C:6](=[O:45])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[N:18]=[C:17]([C:19]3[S:23][C:22]([NH:24]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)=[N:21][C:20]=3[NH2:44])[O:16][N:15]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)=O.C(OCC)C>[C:1]([O:5][C:6](=[O:45])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[N:18]=[C:17]([C:19]3[S:23][C:22]([NH2:24])=[N:21][C:20]=3[NH2:44])[O:16][N:15]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 21358716HCID 21358716, compound

Product 1

HCID 21358705HCID 21358705, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 86584494HCID 86584494, compoundSolvent

Procedure

A solution of 1.3 mmol of (3-{5-[4-amino-2-(trityl-amino)-thiazol-5-yl]-[1,2,4]oxadiazol-3-yl}-phenyl)-carbamic acid tert-butyl ester, prepared as described in Example B(1), dissolved in 8 ml of 1:1 formic acid/diethyl ether was stirred at room temperature until the starting material had been consumed by TLC (typically 5 h). The resulting light yellow solution was stripped of all solvent in vacuo, heated gently under high vacuum to remove residual formic acid, and then recrystallized from methylene chloride, giving 255 mg of the title compound (53% yield) as a light-yellow powder.

Workup

  1. customhad been consumed by TLC (typically 5 h)
  2. temperatureheated gently under high vacuum
  3. customto remove residual formic acid
  4. customrecrystallized from methylene chloride

Sources & evidence

ORD record
ord-475f099eb8144d0db0fe9ca813a092d2
Source dataset
uspto-grants-2003_09
Patent number
US06620828B2

Reaction notes

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