Trifluoroacetic acid → HCID 178517132, compound

HRID 1050374Notes

Reaction equation

HRID 1050374 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8](COCC[Si](C)(C)C)[C:9]2[C:10]3[N:17]=[N:16][N:15](COCC[Si](C)(C)C)[C:11]=3[N:12]=[CH:13][N:14]=2)[C:5](=[O:34])[N:4]2[C:35]3([CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[NH:36][C:37](=[O:38])[C:3]=12.FC(F)(F)C(O)=O.[OH-].[K+]>ClCCl.O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:10]3[N:17]=[N:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[C:5](=[O:34])[N:4]2[C:35]3([NH:36][C:37](=[O:38])[C:3]=12)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 123336796HCID 123336796, compound

Product 1

HCID 178517132HCID 178517132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 8-chloro-6-[2-trimethylsilylethoxymethyl-[3-(2-trimethylsilylethoxymethyl)triazolo[4,5-d]pyrimidin-7-yl]amino]spiro[2H-imidazo[1,5-a]pyridine-3,1′-cyclohexane]-1,5-dione (7, 0.3 g, 0.46 mmol) in dichloromethane (15 mL), trifluoroacetic acid (5 mL, 4.63 mmol) was added drop wise at 0° C. The reaction mass was stirred for overnight at room temperature. After completion, reaction mass was concentrated and co-evaporated with diethyl ether. The crude was then dissolved in tetrahydrofuran/ethanol solution and potassium hydroxide (5 mL, 0.46 mmol) solution (3 M in water) was added and stirred the mixture for 16 h. After completion of the reaction the aqueous layer was separated and organic layer was dried over sodium sulfate, filtered and concentrated to get crude. The crude was washed with methanol and n-pentane and dried to afford 8-chloro-6-(3H-triazolo[4,5-d]pyrimidin-7-ylamino)spiro[2H-imidazo[1,5-a]pyridine-3,1′-cyclohexane]-1,5-dione (Cpd. No. 146) as brown solid. Yield: 70 mg, 39%; MS (ESI) m/z 387.39 [M+1]+; 1H NMR: (400 MHz, DMSO-d6) δ 10.45 (brs, 1H), 9.29 (s, 1H), 8.88 (s, 1H), 7.77 (s, 1H), 2.94 (t, J=2.32, 2H), 1.79-1.76 (m, 2H), 1.67-1.51 (m, 5H), 1.27-1.23 (m, 1H).

Workup

  1. customAfter completion, reaction mass
  2. concentrationwas concentrated and co-evaporated with diethyl ether
  3. dissolutionThe crude was then dissolved in tetrahydrofuran/ethanol solution
  4. stirringstirred the mixture for 16 h
  5. customAfter completion of the reaction the aqueous layer
  6. customwas separated
  7. dry with materialorganic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto get crude
  11. washThe crude was washed with methanol and n-pentane
  12. customdried

Sources & evidence

ORD record
ord-cb84f9d33fa24740a6f7b5af4a46c9dc
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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