Acetic Acid → HCID 178457536, compound

HRID 585506Notes

Reaction equation

HRID 585506 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[C:12](=[O:32])[N:13]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28](SC)=[NH:29])=[CH:23][CH:22]=2)[C:14]3=[O:19])=[O:8])=[CH:4][CH:3]=1.[CH2:33]([NH2:36])[CH2:34]N.[C:37](O)(=O)C>CO.C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[C:12](=[O:32])[N:13]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28](=[NH:29])[NH:36][CH2:33][CH2:34][CH3:37])=[CH:23][CH:22]=2)[C:14]3=[O:19])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 12019538HCID 12019538, compound

Product 1

HCID 178457536HCID 178457536, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

1.5 g (3.1 mmol) of methyl 2-{4-[(4-{[(5-chloro-2-thienyl)carbonyl]amino}-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}ethaneimidothioate are suspended in 190 ml of methanol, and 280 mg (4.65.mmol) of ethylenediamine and 370 mg (6.2 mmol) of acetic acid are added. The mixture is stirred at room temperature overnight, diluted with methanol and methylene chloride until a clear solution is formed and adsorbed on silica gel. Chromatography on silica gel (CH2Cl2/EtOH=10/1 to 3/1) gives 570 mg (31% of theory) of the desired compound. The product is dissolved in methanol and methylene chloride, and trifluoroacetic acid is added. Removal of the solvent under reduced pressure gives the product as trifluoroacetic acid salt. Alternatively, the purification can also be carried out by chromatography on an RP8 silica gel column (water/acetonitrile=4/1+0.1% trifluoroacetic acid to 1/1+0.1% trifluoroacetic acid).

Workup

  1. customis formed

Sources & evidence

ORD record
ord-f7383479df98444698d36b780150d5ce
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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