HCID 86584930, compound → HCID 178502056, compound

HRID 2250731Notes

Reaction equation

HRID 2250731 reaction equation
[CH3:1][O:2][C:3](=[O:20])[NH:4][C:5]1[S:6][C:7]2[C:13]([C:14](=O)[CH2:15]Br)=[CH:12][CH:11]=[C:10]([O:18][CH3:19])[C:8]=2[N:9]=1.[C:21]([O:25][C:26]([NH:28][C:29]([NH2:31])=[NH:30])=[O:27])([CH3:24])([CH3:23])[CH3:22]>C(#N)C>[CH3:1][O:2][C:3](=[O:20])[NH:4][C:5]1[S:6][C:7]2[C:13]([C:14]3[N:31]=[C:29]([NH:28][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[NH:30][CH:15]=3)=[CH:12][CH:11]=[C:10]([O:18][CH3:19])[C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 86584930HCID 86584930, compoundHCID 178454308HCID 178454308, compound

Product 1

HCID 178502056HCID 178502056, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.25 g of (7-bromoacetyl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester (0.0007 Mol) and 0.33 g of tert-butoxycarbonylguanidine (0.0021 Mol) were heated to reflux in acetonitril (3 ml) for 3 hrs. After evaporation of the solvent the residue was triturated with water (10 ml) and filtered. The filtrate was evaporated and the residue subjected to column chromatography (silicagel, ethyl-acetate/hexanes 1:1) to yield the title compound as a white solid (17%); F.p.: 255-265° C.

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas triturated with water (10 ml)
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-2d773209063c4fe891254d64927afac0
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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