Trifluoroacetic acid → HCID 59472160, compound

HRID 78616Notes

Reaction equation

HRID 78616 reaction equation
C(OC([N:8]([C:16]1[C:21]([C:22]2[O:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:25][N:26]=2)=[N:20][C:19]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][C:38]=2[C:39]#[N:40])=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][C:16]1[N:17]=[CH:18][C:19]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][C:38]=2[C:39]#[N:40])=[N:20][C:21]=1[C:22]1[O:23][C:24]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:25][N:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59472419HCID 59472419, compound

Product 1

HCID 59472160HCID 59472160, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl N-tert-butoxycarbonyl-N-[5-(4-cyano-3-pyridyl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]carbamate (140 mg, 0.2585 mmol) in dichloromethane (2 mL) was treated with TFA (2 mL, 25.96 mmol) and stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure, re-dissolved in MeOH/DCM and concentrated (2×), dissolved MeOH/DCM and passed through bicarbonate cartridge, concentrated under reduced pressure to give a yellow solid. The solid was triturated with acetonitrile and filtered to give yellow solid (83 mg, 94%); 1H NMR (400.0 MHz, DMSO) d 7.69-7.77 (m, 3H), 8.07 (d, 1H), 8.24-8.26 (m, 2H), 7.80-8.40 (br s, 2H), 8.90 (d, 1H), 9.09 (s, 1H) and 9.47 (s, 1H) ppm; MS (ES+) 342.16

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionre-dissolved in MeOH/DCM
  3. concentrationconcentrated (2×)
  4. dissolutiondissolved MeOH/DCM
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow solid
  7. customThe solid was triturated with acetonitrile
  8. filtrationfiltered

Sources & evidence

ORD record
ord-3f41045d062e4553a12fe28fa55ee4dc
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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