Trifluoroacetic acid methylene chloride → HCID 86591043, compound

HRID 1592013Notes

Reaction equation

HRID 1592013 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:10](=[O:11])[CH2:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[NH2:19])[S:7]1(=[O:21])=[O:20].[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29].C(Cl)Cl>>[OH:34][C:28]([C:30]([F:33])([F:32])[F:31])=[O:29].[NH2:19][C:13]1[CH:14]=[C:15]([NH2:18])[CH:16]=[CH:17][C:12]=1[N:8]1[S:7](=[O:21])(=[O:20])[NH:6][C:10](=[O:11])[CH2:9]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 67139584HCID 67139584, compound

Product 1

HCID 86591043HCID 86591043, compound

Procedure

A solution of the title D compound, 2-(2,4-dimethoxybenzyl)-5-(2,4-diaminophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (40 mg, 0.10 mmol) is stirred in 4 mL of TFA/CH2Cl2 (1:1) at RT for 16 h. The volatiles are evaporated and the residue is stirred in 4 mL of MeCN/water (1:1) for 20 min. The mixture is filtered through a 0.2 μM Acrodisc and the solvents are evaporated. The residue is triturated from diethylether (Et2O) to give 5-(2,4-diaminophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one TFA salt as a brown solid: [M+1]+=243.

Workup

  1. customThe volatiles are evaporated
  2. filtrationThe mixture is filtered through a 0.2 μM Acrodisc
  3. customthe solvents are evaporated
  4. customThe residue is triturated from diethylether (Et2O)

Sources & evidence

ORD record
ord-fcc2ea34487048328584119dcb28c710
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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