HCID 136076169, compound → HCID 135659592, compound

HRID 2289256Notes

Reaction equation

HRID 2289256 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:17]([NH:20][C:21]4[CH:42]=[CH:41][C:24]([C:25]([NH:27][C@H:28]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:26])=[CH:23][CH:22]=4)(=[O:19])=[O:18])[CH:15]=[CH:16][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1>COCCOCCOC.[Pd]>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:17]([NH:20][C:21]4[CH:22]=[CH:23][C:24]([C:25]([NH:27][C@H:28]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:26])=[CH:41][CH:42]=4)(=[O:19])=[O:18])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 136076169HCID 136076169, compound

Product 1

HCID 135659592HCID 135659592, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8150DiglymeSolvent2×

Procedure

A solution of diethyl N-(4-((1,2,5,6-tetrahydro-3-methyl-1-oxo-benzo-[f]quinazolin-9-yl) sulfonamido)benzoyl)-L-glutamate (0.50 g, 0.84 mmol) in diglyme (10 ml) was stirred with 10% palladium on carbon (0.25 g) (Aldrich) under nitrogen at reflux for 3 hours. The solution was diluted with diglyme (20 ml), filtered hot through celite, and concentrated under high vacuum. The resulting solid was suspended in hot methanol (50 ml), stirred overnight at room temperature, filtered, and dried under high vacuum to give diethyl N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)sulfonamido)benzoyl)-L-glutamate as a white solid (0.25 g). 1H NMR (DMSO-d6, 200 MHz) δ: 1.10 (t, J=7 Hz, 3H, ester CH3), 1.12 (t, J=7 Hz, 3H, ester CH3), 1.78-2.15 (m, 2H, glu CH2), 2.35 (t, J=7 Hz, 2H, glu CH2), 2.4 3 (s, 3H, C3 --CH3), 3.98 (q, J=7 Hz, 2H, ester CH2), 4.04 (q, J=7 Hz, 2H, ester CH2), 2.35-4.39 (m, 1H, glu CH), 7.21 (d, J=9 Hz, 2H, Ar), 7.69 (d, J=9 Hz, 2H, Ar), 7.76 (d, J=9 Hz, 1H, Ar), 7.91 (dd, J=9,2 Hz, 1H, Ar), 8.19 (d, J=9 Hz, 1H, Ar), 8.29 (d, J 9 Hz, 1H, Ar), 8.51 (d, J=7 Hz, 1H, glu NH), 10.44 (d, J=2 Hz, 1H, Ar), 10.88 (br s, 1H, SO2NH), 12.75 (br s, 1H, N2H). Mass spectrum (CI-CH4): 595 (M+1, 24.1%). Anal. Calculated for C29H30N4O8S: C, 58.58; H, 5.08; N, 9.42; S, 5.39. Found: C, 58.46; H, 5.10; N, 9.34; S, 5.41.

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationfiltered hot through celite
  3. concentrationconcentrated under high vacuum
  4. filtrationfiltered
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-d23fbf65ddaa40d4bba649105492ec71
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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