Trifluoroacetic acid → HCID 21914341, compound

HRID 2421369Notes

Reaction equation

HRID 2421369 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[S:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].FC(F)(F)C(O)=O>ClCCl.CO>[NH2:1][C:2]([NH:4][C:5]1[S:6][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21914463HCID 21914463, compound

Product 1

HCID 21914341HCID 21914341, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-[(Aminocarbonyl)amino]-5-[2-(4-t-butyloxycarbonylpiperazin-1-yl)phenyl]thiophene-3-carboxamide (64 mg) was stirred in dichloromethane (4 ml). Trifluoroacetic acid (1 ml) was added and the solution was stirred at room temperature for 1 h. The volatile materials were removed in vacuo; the residue was diluted with water (2 ml) and basified with a few drops of aqueous ammonia. The precipitated product was collected by filtration and washed with water. The gummy solid obtained was dissolved in methanol, the solvent was evaporated and the residue triturated with a mixture of methanol and ether and then filtered to give the product as an off-white solid (20 mg).

Workup

  1. customThe volatile materials were removed in vacuo
  2. additionthe residue was diluted with water (2 ml)
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with water
  5. customThe gummy solid obtained
  6. customthe solvent was evaporated
  7. customthe residue triturated with a mixture of methanol and ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-248ab7c76f9e49819250369dfc877e1f
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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