Trifluoroacetic acid → HCID 756604, compound

HRID 2176430Notes

Reaction equation

HRID 2176430 reaction equation
[CH2:1]([C:3]1[S:25][C:6]2=[N:7][C:8]([N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)=[CH:9][C:10](=[O:11])[N:5]2[N:4]=1)[CH3:2].FC(F)(F)C(O)=O>ClCCl.CO>[CH2:1]([C:3]1[S:25][C:6]2=[N:7][C:8]([N:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)=[CH:9][C:10](=[O:11])[N:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66668105HCID 66668105, compound

Product 1

HCID 756604HCID 756604, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-ethyl-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (3.39 g, 9.28 mmol, 1.0 equiv) in 40 mL of dichloromethane is added trifluoroacetic acid (10 ml, 130 mmol, 14 equiv). The mixture stirred for 18 h, after which it is concentrated in vacuo and azeotroped with dichloroethane to give a yellow solid. The crude residue is dissolved in MeOH and purified by HPLC to give 2-ethyl-7-(piperazin-1-yl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (2.053 g, 83% yield) as an off-white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 5.30 (s, 1H), 3.37-3.44 (m, 4H), 2.94 (q, J=7.56 Hz, 2H), 2.64-2.73 (m, 4H), 1.25 (t, 3H); LCMS: (electrospray+ve), m/z 266.0 (MH)+; HPLC: tR=2.71 min, UV254=100%. HRMS (ESI): m/z calcd for C11H16N5OS [M+H]+266.1069. found 266.1073.

Workup

  1. concentrationafter which it is concentrated in vacuo
  2. customazeotroped with dichloroethane
  3. customto give a yellow solid
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-d2873c0101074c3aa24804db9a633897
Source dataset
uspto-grants-2015_06
Patent number
US09066948B2

Reaction notes

Loading…