HCID 57639516, compound → HCID 178516240, compound

HRID 2091650Notes

Reaction equation

HRID 2091650 reaction equation
[CH:1]1([N:6]2[C:14]([NH:15][C:16]3[C:21]([F:22])=[CH:20][C:19]([F:23])=[CH:18][C:17]=3[F:24])=[N:13][C:12]3[C:7]2=[N:8][C:9]([NH:25][C:26]2[CH:27]=[N:28][C:29]([O:32]C)=[CH:30][CH:31]=2)=[N:10][CH:11]=3)[CH2:5][CH2:4][CH2:3][CH2:2]1>Br.C(O)(=O)C>[CH:1]1([N:6]2[C:14]([NH:15][C:16]3[C:21]([F:22])=[CH:20][C:19]([F:23])=[CH:18][C:17]=3[F:24])=[N:13][C:12]3[C:7]2=[N:8][C:9]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[N:28][CH:27]=2)=[N:10][CH:11]=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 1

HCID 57639516HCID 57639516, compound

Product 1

HCID 178516240HCID 178516240, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Conditions

Temperature
80 °C

Procedure

9-Cyclopentyl-N2-(6-methoxypyridin-3-yl)-N8-(2,4,6-trifluorophenyl)-9H-purine-2,8-diamine (0.350 g., 0.769 mmol) was dissolved in 30% HBr/acetic acid in a sealed tube and heated to 80° C. for 16 hours. Product confirmed by LC-MS. The solution was partitioned between 1.75 M potassium carbonate and ethyl acetate (3×). The organics were combined, dried over magnesium sulfate, filtered and solvent removed under reduced pressure. The resultant solid was purified via preparative HPLC (5-55% acetonitrile/water, 20 mL/min.) to afford the title compound (0.212 g, 34%). ES-MS (m/z) 442 [M+1]+. Melting point 257-260° C.

Workup

  1. customThe solution was partitioned between 1.75 M potassium carbonate and ethyl acetate (3×)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customsolvent removed under reduced pressure
  5. customThe resultant solid was purified via preparative HPLC (5-55% acetonitrile/water, 20 mL/min.)

Sources & evidence

ORD record
ord-0c36fed8b29149f9ba4c0e2c90c00c17
Source dataset
uspto-grants-2013_05
Patent number
US08440661B2

Reaction notes

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