Reaction #475271

Reaction equation

1-Cyclopentylmethyl-6-(5-isopropyl-2-methoxy-phenyl)-1,3-dihydro-imidazo[4,5-b]pyrazin-2-one

cyclopentylmethylamine

→

solid

Yield 75.0%

1-CYCLOPENTYLETHYL-6-(5-ISOPROPYL-2-METHOXY-PHENYL)-1,3-DIHYDRO-IMIDAZO[4,5-B]PYRAZIN-2-ONE

Yield 75.0%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe product was purified
2. 2
   Otherreverse-phase semi-preparatory HPLC (5-70% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)
3. 3
   ConcentrationProduct fractions were concentrated
4. 4
   Othertriturated with 50% methanol in H2O

Procedure

1-Cyclopentylmethyl-6-(5-isopropyl-2-methoxy-phenyl)-1,3-dihydro-imidazo[4,5-b]pyrazin-2-one. N-Bis-Boc-3-bromo-5-(5-isopropyl-2-methoxy-phenyl)-pyrazin-2-ylamine (see Example 5.C) (150 mg, 0.29 mmol), cyclopentylmethylamine (0.287 mL, 2.9 mmol) and ethanol (4 mL) were heated according to General Procedure E. The product was purified using reverse-phase semi-preparatory HPLC (5-70% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). Product fractions were concentrated and then triturated with 50% methanol in H2O to give a white solid (77 mg, 75% yield). 1H NMR (300 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.36 (s, 1H), 7.60 (d, J=2.5, 1H), 7.26 (dd, J=8.7, 2.6, 1H), 7.08 (d, J=8.5, 1H), 3.82 (s, 3H), 3.78 (d, J=7.4, 2H), 2.45 (d, J=7.1, 1H), 1.58-1.70 (m, 4H), 1.53 (d, J=9.3, 2H), 1.38 (d, J=4.4, 2H), 1.22 (d, J=6.9, 6H); MS (ESI) m/z 367.5 [M+1]+.

Source