Cyclopentanemethylamine → 1-Cyclopentylethyl-6-(5-isopropyl-2-methoxy-phenyl)-1,3-dihydro-imidazo[4,5-B]pyrazin-2-one

HRID 388089

Reaction equation

HRID 388089 reaction equation
[CH:1]1([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[C:20]([CH:22]([CH3:24])[CH3:23])[CH:19]=[CH:18][C:17]=4[O:25][CH3:26])=[CH:14][N:15]=[C:10]3[NH:9][C:8]2=[O:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:28]1(CN)CCCC1>C(O)C>[CH:1]1([CH:6]([N:7]2[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[C:20]([CH:22]([CH3:23])[CH3:24])[CH:19]=[CH:18][C:17]=4[O:25][CH3:26])=[CH:14][N:15]=[C:10]3[NH:9][C:8]2=[O:27])[CH3:28])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 80153CyclopentanemethylamineHCID 249848491-Cyclopentylmethyl-6-(5-isopropyl-2-methoxy-phenyl)-1,3-dihydro-imidazo[4,5-b]pyrazin-2-one

Product 1

HCID 674333041-Cyclopentylethyl-6-(5-isopropyl-2-methoxy-phenyl)-1,3-dihydro-imidazo[4,5-B]pyrazin-2-oneYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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]+.

Workup

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

Sources & evidence

ORD record
ord-99d4ee393eda4ba48aa5a2ae60cc125e
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Linked notes

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