Diisopropylethylamine → HCID 178462584, compound

HRID 243278Notes

Reaction equation

HRID 243278 reaction equation
Cl.Cl.[CH2:3]([N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH:14]([NH2:16])[CH3:15])[CH3:4].Cl[C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][NH:22]2.CCN(C(C)C)C(C)C>C(O)CCC>[CH2:3]([N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH:14]([NH:16][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][NH:22]2)[CH3:15])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 470022201-(1-ethyl-1H-1,3-benzodiazol-2-yl)ethan-1-amine dihydrochlorideHCID 178478393HCID 178478393, compound

Product 1

HCID 178462584HCID 178462584, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(1-ethyl-1H-1,3-benzodiazol-2-yl)ethan-1-amine dihydrochloride (346 mg, 1.32 mmol), 6-chloro-9H-purine (204 mg, 1.32 mmol) and DIPEA (904 μL, 5.28 mmol) in n-butanol (2.5 mL) was stirred in a sealed tube for 3 h at 120° C. After cooling to RT, the crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) and triturated with a mixture EtOAc/diethyl ether, filtered and further washed with additional diethyl ether affording racemic 107 as a pale pink solid (182 mg, 45%). LCMS: RT 2.18 min [M+H]+ 308.1. 1H NMR (CDCl3, 400 MHz): δ 8.51 (1H, s), 7.95 (1H, s), 7.76 (1H, d, J=7.17 Hz), 7.39-7.34 (1H, m), 7.31-7.15 (3H, m), 6.03 (1H, br), 4.51-4.39 (1H, m), 4.37-4.26 (1H, m), 1.97-1.80 (4H, m), 1.43 (3H, t, J=7.21 Hz)

Workup

  1. temperatureAfter cooling to RT
  2. customthe crude reaction mixture
  3. washwas washed with MeOH
  4. washthe product eluted with 2M NH3/MeOH
  5. additionThe product containing fractions
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)
  8. customtriturated with a mixture EtOAc/diethyl ether
  9. filtrationfiltered
  10. washfurther washed with additional diethyl ether affording racemic 107 as a pale pink solid (182 mg, 45%)

Sources & evidence

ORD record
ord-d41b96684d6b4784ad24bc6d65d3d194
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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