Chlorotrimethylsilane → 4-(10-methyl-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)-butyronitrile

HRID 2393403Notes

Reaction equation

HRID 2393403 reaction equation
[CH3:1][C:2]1([CH2:19][CH2:20][CH2:21][CH2:22]C(OCC)=O)[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.CC1C2N3C=CN=C3C(=O)[NH:37]C=2C2C=CC=CC1=2.[H-].[Na+].C[Si](Cl)(C)C.BrCCCC#N>CN(C)C=O>[CH3:1][C:2]1([CH2:19][CH2:20][CH2:21][C:22]#[N:37])[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 214124-BromobutyronitrileHCID 24758Sodium hydrideHCID 18975437ethyl 5-(10-methyl-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-10-yl)valerateHCID 1897544610-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 189754224-(10-methyl-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)-butyronitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The process is performed as in Example 50 for the preparation of ethyl 5-(10-methyl-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)-valerate but starting with 1.42 g of 10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 75 ml of dimethylformamide, 1 g of sodium hydride, 0.84 ml of trimethylsilyl chloride and 0.76 ml of 4-bromo-butyronitrile. The product is first purified by crystallization from acetonitrile, then by heating of the crystals to reflux in an ethyl acetate/methanol mixture (9/1 by volume). After allowing to stand for 2 hours at a temperature in the region of 20° C., the suspension is filtered and the solid is washed with ethyl acetate and dried at 60° C. under vacuum (1 mmHg; 0.13 kPa). 0.83 g of 4-(10-methyl-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)-butyronitrile is obtained in the form of an off-white solid melting above 260° C. (Analysis, % calculated C: 71.04, H: 5.30, N: 18.41, O: 5.26, % found C: 70.7, H: 5.5, N: 18.6).

Workup

  1. customThe product is first purified by crystallization from acetonitrile
  2. temperatureby heating of the crystals
  3. temperatureto reflux in an ethyl acetate/methanol mixture (9/1 by volume)
  4. filtrationthe suspension is filtered
  5. washthe solid is washed with ethyl acetate
  6. customdried at 60° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-31401a9e271c4ff5897fa20c8d0c4618
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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