Trifluoroacetic acid → HCID 178509092, compound

HRID 555243Notes

Reaction equation

HRID 555243 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[N:17]=[C:16]2[C:12]([NH:13][CH:14]=[N:15]2)=[C:11](Cl)[N:10]=1.C([N:22](CC)C(C)C)(C)C>C(O)(C)C>[Cl:8][C:9]1[NH:10][C:11]([NH2:22])=[C:12]2[C:16]([N:17]=1)=[N:15][CH:14]=[N:13]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 53244122,6-Dichloropurine

Product 1

HCID 178509092HCID 178509092, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A glass tube was charged with the above amount of TFA salt 13, commercially available 2,6-dichloropurine (1.02 g, 5.43 mmol), N,N-diisopropylethylamine (DIPEA, 3.14 mL, 4.96 mmol) and isopropyl alcohol (IPA, 6 mL). The glass tube was sealed and then shaken at 100° C. for 17 hours. The volatiles were evaporated and the resulting residue was purified by flash chromatography eluting with ethyl acetate-methanol (100:5, including 1% triethylamine) to afford 1.25 g of mono-SNAR product 14, racemic-(2-exo,3-exo-)-N6[3-(dimethylamino)carbonylbicyclo-[2.2.1]hept-5-en-2-yl)]-2-chloro-1H-purine-6-amine, in 70% yield. 1H NMR (300 MHz, CD3OD) δ: 8.05 (s, 1H), 6.35 (m, 2H), 4.68 (m, 1H), 3.00 (s, 1H), 3.04 (s, 1H), 3.00 (s, 3H), 2.95 (s, 1H), 2.83 (s, 1H), 2.68 (s, 3H), 2.39 (d, J=8.7 Hz, 1H), 1.69 (d, J=9.0 Hz, 1H), 1.33 (m, 1H); LC-MS: purity: 90.51%; MS (m/e): 333.43 (M+H)+.

Workup

  1. customThe glass tube was sealed
  2. customThe volatiles were evaporated
  3. customthe resulting residue was purified by flash chromatography
  4. washeluting with ethyl acetate-methanol (100:5, including 1% triethylamine)

Sources & evidence

ORD record
ord-fe990c6f6fca4c2ba8515d8f39c0a2f0
Source dataset
uspto-grants-2011_11
Patent number
US08053434B2

Reaction notes

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