Trifluoroacetic acid → HCID 86753022, compound

HRID 482099Notes

Reaction equation

HRID 482099 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([O:26][S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])(=[O:29])=[O:28])[CH:19]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:21]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.Cl.[N:45]1(C(N)=N)C=CC=[N:46]1>C(Cl)Cl>[NH2:45][N:46]=[CH:6][N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([O:26][S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])(=[O:28])=[O:29])[CH:19]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:21]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2734672Pyrazole-1-carboxamidine monohydrochloride2×HCID 86753021HCID 86753021, compound

Product 1

HCID 86753022HCID 86753022, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chlorobenzenesulfonic acid 3 -[[1-N-(tert-butoxycarbonyl)piperidin-4-yl]methoxy]-5-carbomethoxyphenyl ester (0.14 g, 0.26 mmol), as prepared in the preceding step, was treated with 2.5 mL of 25% trifluoroacetic acid in methylene chloride at ambient temperature for 15 min. The solvent was evaporated, the residue was azeotroped with acetonitrile (2 times), and placed under high vacuum. The residue was dissolved in methanol (3 mL) and treated with 1H-pyrazole-1-carboxamidine hydrochloride (0.057 g, 0.39 mmol) and N,N-duisopropylethylamine (0.136 mL, 0.78 mmol). The reaction mixture was stirred at ambient temperature overnight. An additional portion of 1H-pyrazole-1-carboxamidine hydrochloride (10 mg) was added to the reaction mixture and then was stirred for 6 h. The solvent was evaporated to dryness. The residue was triturated with hexane and ether. The residue was dissolved in acetonitrile and diluted with diethylether to produce a crystalline crop, which was collected by filtration to give 25.3 mg of solid. 1H-NMR (CDCl3 ; 300 MHz): δ 1.44-1.55 (m, 2H), 1.95-2.1 (m, 3H ), 3.11 (t, 2H ), 3.81 (d, 2H), 3.87 (s, 3H), 4.07 (d, 2H), 6.90 (t, 1H), 7.38 (m, 5H), 7.64 (m, 2H), 7.96 (m, 1H). Mass spectrum MADLDI-TOF) calcd. for C21H24N3O6SCl: 482.1 (M+H). Found 483.5.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was azeotroped with acetonitrile (2 times)
  3. dissolutionThe residue was dissolved in methanol (3 mL)
  4. stirringwas stirred for 6 h
  5. customThe solvent was evaporated to dryness
  6. customThe residue was triturated with hexane and ether
  7. dissolutionThe residue was dissolved in acetonitrile
  8. additiondiluted with diethylether
  9. customto produce a crystalline crop, which
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-891f4f408e0443bf9c9fb0aeec52f07c
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

Loading…