HCID 57681536, compound → HCID 23131095, compound

HRID 493707Notes

Reaction equation

HRID 493707 reaction equation
[Br:1][C:2]1[S:6]/[C:5](=[N:7]\C(=O)OC(C)(C)C)/[N:4]([CH3:15])[C:3]=1[CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:40])[CH2:24][CH2:25][S:26]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([Cl:39])[CH:35]=3)[CH:30]=2)(=[O:28])=[O:27])[CH2:19][CH2:18]1>FC(F)(F)C(O)=O>[Br:1][C:2]1[S:6][C:5](=[NH:7])[N:4]([CH3:15])[C:3]=1[CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:40])[CH2:24][CH2:25][S:26]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([Cl:39])[CH:35]=3)[CH:30]=2)(=[O:27])=[O:28])[CH2:19][CH2:18]1

Participants

3

Reactant 1

HCID 57681536HCID 57681536, compound

Product 1

HCID 23131095HCID 23131095, compoundYield 6.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl ((2Z)-5-bromo-4-((4-(3-((6-chloro-2-naphthyl)sulfonyl)propanoyl)-1-piperazinyl)methyl)-3-methyl-1,3-thiazol-2(3H)-ylidene)carbamate (1.2 g) obtained in Example 30c) was dissolved in trifluoroacetic acid (10 mL), and the mixture was mixed at room temperature for 1 hour. The solvent was distilled off, and the residue was poured into an aqueous potassium carbonate solution. The mixture was extracted with a mixed solution of chloroform-methanol, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified with a basic silica gel column to give the title compound (0.07 g) as a pale brown powder.

Workup

  1. additionthe mixture was mixed at room temperature for 1 hour
  2. distillationThe solvent was distilled off
  3. additionthe residue was poured into an aqueous potassium carbonate solution
  4. extractionThe mixture was extracted with a mixed solution of chloroform-methanol
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified with a basic silica gel column

Sources & evidence

ORD record
ord-fc6645c80c9c4811b2cdb59d97476714
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

Loading…