1,1'-Carbonyldiimidazole → HCID 24985359, compound

HRID 388100Notes

Reaction equation

HRID 388100 reaction equation
[C:1]1([CH:7]([NH:9][C:10]2[C:11](=[O:26])[NH:12][CH:13]=[C:14]([C:16]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:17]=3[CH:18]=[CH:19][CH:20]=[N:21]4)[N:15]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28]>O1CCOCC1>[C:1]1([CH:7]([N:9]2[C:10]3=[N:15][C:14]([C:16]4[CH:25]=[CH:24][CH:23]=[C:22]5[C:17]=4[CH:18]=[CH:19][CH:20]=[N:21]5)=[CH:13][N:12]=[C:11]3[O:26][C:27]2=[O:28])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 66699912HCID 66699912, compound

Product 1

HCID 24985359HCID 24985359, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(1-Phenyl-ethyl)-5-quinolin-5-yl-3H-oxazole[4,5-b]pyrazin-2-one. 3-(1-Phenyl-ethylamino)-5-quinolin-5-yl-1H-pyrazin-2-one (50 mg, 0.15 mmol), 1,1′-carbonyldiimidazole (470 mg, 1.5 mmol), and dioxane (5 mL) were heated together in a pressure tube to 150° C. for 20 hours. The reaction was filtered through celite, rinsed with EtOAc, and then concentrated. The residue was purified via Biotage silica gel chromatography (0-100% ethyl acetate in hexanes). The product factions were concentrated and then triturated with ether to give a white solid, (28 mg, 52% yield). 1H NMR (400 MHz, CD3OD) δ 9.73 (dd, J=4.1, 1.8, 1 H), 9.11 (s, 1 H), 9.09 (d, J=8.2, 1 H), 8.93 (d, J=8.6, 1 H), 8.66 (m, 1 H), 8.58 (dd, J=7.2, 1.4, 1 H), 8.31 (m, 2 H), 8.26 (dd, J=8.6, 4.3, 1 H), 8.17 (m, 2 H), 6.43 (q, J=7.0, 1 H), 2.71 (d, J=7.0, 3 H); MS (ESI) m/z 369.4 [M+1]+.

Workup

  1. filtrationThe reaction was filtered through celite
  2. washrinsed with EtOAc
  3. concentrationconcentrated
  4. customThe residue was purified via Biotage silica gel chromatography (0-100% ethyl acetate in hexanes)
  5. concentrationThe product factions were concentrated
  6. customtriturated with ether
  7. customto give a white solid, (28 mg, 52% yield)

Sources & evidence

ORD record
ord-aeda3fe49a194ba7a025a3061c52fa91
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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