Hydrochloric Acid → HCID 22283321, compound

HRID 2250735Notes

Reaction equation

HRID 2250735 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:7][C:8]1[CH:52]=[CH:51][C:11]([C:12]([NH:14][C:15]2[S:16][C:17]3[C:23]([C:24]4[N:25]=[C:26]([NH:29]C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[S:27][CH:28]=4)=[CH:22][CH:21]=[C:20]([O:49][CH3:50])[C:18]=3[N:19]=2)=[O:13])=[CH:10][CH:9]=1)[CH3:6].Cl>CO>[NH2:29][C:26]1[S:27][CH:28]=[C:24]([C:23]2[C:17]3[S:16][C:15]([NH:14][C:12](=[O:13])[C:11]4[CH:10]=[CH:9][C:8]([CH2:7][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:6])=[CH:52][CH:51]=4)=[N:19][C:18]=3[C:20]([O:49][CH3:50])=[CH:21][CH:22]=2)[N:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22283161HCID 22283161, compound

Product 1

HCID 22283321HCID 22283321, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

g of 4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-N-{4-methoxy-7-[2-(trityl-amino)-thiazol-4-yl]-benzothiazol-2-yl}-benzamide (0.00014 Mol) were treated with cc HCl (0.03 ml) in MeOH (1 ml) for 1 h at reflux. After evaporation of the solvent the residue was taken up in water (10 ml), treated with sat. NaHCO3 (10 ml) and extracted 4× with ethyl acetate. The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was subjected to column chromatography (silicagel, ethyl acetate, CH2Cl2/MeOH 19:1 and 9:1). The title compound was obtained as a white solid (53%); F.p.: 199-206° C.

Workup

  1. temperatureat reflux
  2. customAfter evaporation of the solvent the residue
  3. additiontreated with sat. NaHCO3 (10 ml)
  4. extractionextracted 4× with ethyl acetate
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fbef9e1c18134fd3ab6fcd811908a299
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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