Trifluoroacetic acid → HCID 59026820, compound

HRID 658367Notes

Reaction equation

HRID 658367 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][NH:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])=[N:11][N:10]=2)[CH2:4][O:3]1.C(O)(C(F)(F)F)=O>ClCCl>[F:28][C:22]1[CH:23]=[C:24]([I:27])[CH:25]=[CH:26][C:21]=1[NH:20][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[C:12]1[O:13][C:9]([NH:8][CH2:7][CH:5]([OH:6])[CH2:4][OH:3])=[N:10][N:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59026839HCID 59026839, compound

Product 1

HCID 59026820HCID 59026820, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-{5-[(2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-amino]-[1,3,4]oxadiazol-2-yl}-pyridin-3-yl)-(2-fluoro-4-iodo-phenyl)-amine (100 mg, 0.2 mmol) was dissolved in dichloromethane (5 mL) and TFA (3 mL) was added. The reaction mixture was stirred at RT for 4 hrs. The solvent was evaporated, and the residue was dissolved in Ethyl acetate, and washed with 1N aqueous NaOH. After solvent evaporation a residue was collected and dissolved in methanol. The product crystallized out the methanolic solution and filtered (63 mg). LC/MS (Method A) [6.61 min; 472(M+1)].

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in Ethyl acetate
  3. washwashed with 1N aqueous NaOH
  4. customAfter solvent evaporation a residue
  5. customwas collected
  6. dissolutiondissolved in methanol
  7. customThe product crystallized out the methanolic solution
  8. filtrationfiltered (63 mg)
  9. customLC/MS (Method A) [6.61 min; 472(M+1)]

Sources & evidence

ORD record
ord-ce8e171cc9b9445bb3dd0d33d20690a3
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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