Trifluoroacetic acid → HCID 118598585, compound

HRID 1050353Notes

Reaction equation

HRID 1050353 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:17]=[CH:16][N:15]=[C:14]3[C:10]=2[N:11](COCC[Si](C)(C)C)[CH:12]=[N:13]3)[C:5](=[O:26])[N:4]2[C:27]3([CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[NH:28][C:29](=[O:30])[C:3]=12.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:17]=[CH:16][N:15]=[C:14]3[C:10]=2[NH:11][CH:12]=[N:13]3)[C:5](=[O:26])[N:4]2[C:27]3([NH:28][C:29](=[O:30])[C:3]=12)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 123745674HCID 123745674, compound

Product 1

HCID 118598585HCID 118598585, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Chloro-6-[[7-(2-trimethylsilylethoxy)purin-6-yl]amino]spiro[2H-imidazo[1,5-a]pyridine-3,1′-cyclohexane]-1,5-dione (5, 0.6 g, 1.2 mmol) was dissolved in dichloromethane (10 mL) in a flask and trifluoroacetic acid (1.36 g, 11.95 mmol) was added dropwise and stirred the mixture at room temperature overnight. After completion, evaporated the solvent under reduced pressure and the crude was basified by saturated aqueous solution of sodium bicarbonate to pH 8 and extracted with dichloromethane (2×50 mL). The organic layer was dried over any. Sodium sulfate and concentrated to afford crude. The crude was purified by flash column chromatography eluting with 2.5% methanol in dichloromethane. The desired fractions were concentrated to dryness under vacuum to afford 8-chloro-6-(7H-purin-6-ylamino)spiro[2H-imidazo[1,5-a]pyridine-3,1′-cyclohexane]-1,5-dione (Cpd. No. 117) as a yellow solid. Yield: 0.06 g, 13%; MS (ESI) m/z 386.39 [M+1]+; 1H NMR: (400 MHz, DMSO-d6) δ 10.43 (m, 1H), 10.37 (s, 1H), 8.88 (s, 1H), 8.64 (s, 1H), 8.43 (s, 1H), 2.94 (t, J=2.32 Hz, 2H), 1.77 (m, 2H), 1.63 (m, 3H), 1.57 (d, J=12.8 Hz, 2H), 1.23 (m, 1H).

Workup

  1. customAfter completion, evaporated the solvent under reduced pressure
  2. extractionextracted with dichloromethane (2×50 mL)
  3. customThe organic layer was dried over any
  4. concentrationSodium sulfate and concentrated
  5. customto afford crude
  6. customThe crude was purified by flash column chromatography
  7. washeluting with 2.5% methanol in dichloromethane
  8. concentrationThe desired fractions were concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-36e3e8129bb14ecbae10caed43567fec
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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