Sodium hydride → HCID 89793699, compound

HRID 1056299Notes

Reaction equation

HRID 1056299 reaction equation
[C:1]([NH:5][C:6]1[C:7]([CH3:24])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[CH:17]=[C:18]([C:21]([NH2:23])=[O:22])[NH:19][CH:20]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].N1([C:30](N2C=CN=C2)=[O:31])C=CN=C1.[H-].[Na+]>C1COCC1.CN(C=O)C>[C:1]([NH:5][C:6]1[C:7]([CH3:24])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[CH:17]=[C:18]3[C:21](=[O:22])[NH:23][C:30](=[O:31])[N:19]3[CH:20]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 682631,1'-Carbonyldiimidazole3×HCID 897842594-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-2-carboxamide

Product 1

HCID 89793699HCID 89793699, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 4-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-2-carboxamide (Example 420; 21.8 mg, 0.067 mmol), di(1H-imidazol-1-yl)methanone (CDI; Aldrich; 12.02 mg, 0.074 mmol), and NaH (60% w/w in mineral oil; 3.24 mg, 0.081 mmol) in a mixture of THF (1.0 mL) and DMF (0.10 mL) was stirred under argon at 23° C. for 1 h. Additional di(1H-imidazol-1-yl)methanone (12 mg, 0.074 mmol) was added, and the resulting mixture was stirred at 23° C. for 5 min. Additional di(1H-imidazol-1-yl)methanone (72 mg, 0.444 mmol) was added, and the resulting mixture was stirred at 23° C. for 5 min. The reaction mixture was subsequently concentrated onto silica gel and chromatographically purified (silica gel, 0-100% EtOAc/hexanes) to provide 6-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione (11.9 mg, 0.034 mmol, 51% yield) as a light-yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.06 (1H, s), 7.82 (1H, d, J=7.6 Hz), 7.66 (1H, dd, J=7.3, 1.3 Hz), 7.40 (1H, d, J=7.6 Hz), 7.32 (1H, d, J=0.7 Hz), 7.30 (0.5; H, br. s), 4.76 (1H, s), 4.05 (0.5; H, s), 2.56 (3H, s), 1.57 (9H, s). m/z (ESI, +ve) 350.0 (M+H)+.

Workup

  1. stirringthe resulting mixture was stirred at 23° C. for 5 min
  2. stirringthe resulting mixture was stirred at 23° C. for 5 min
  3. concentrationThe reaction mixture was subsequently concentrated onto silica gel
  4. customchromatographically purified (silica gel, 0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-beae44b3ef624c79aaa9f060d2165eea
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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