Diisopropylethylamine → Benzyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]sulfonyl}-2-methylpiperazine-1-carboxylate

HRID 394204Notes

Reaction equation

HRID 394204 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].C(N(C(C)C)CC)(C)C.[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:43]=[C:42]([S:44](Cl)(=[O:46])=[O:45])[CH:41]=[C:40]2[C:35]=1[CH2:36][N:37]([CH2:57][C:58]1[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][CH:59]=1)[C:38](=[O:56])[N:39]2[C:48]1[C:53]([Cl:54])=[CH:52][CH:51]=[CH:50][C:49]=1[Cl:55]>C1COCC1>[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:43]=[C:42]([S:44]([N:6]2[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH:2]([CH3:1])[CH2:7]2)(=[O:46])=[O:45])[CH:41]=[C:40]2[C:35]=1[CH2:36][N:37]([CH2:57][C:58]1[CH:59]=[CH:60][C:61]([O:64][CH3:65])=[CH:62][CH:63]=1)[C:38](=[O:56])[N:39]2[C:48]1[C:49]([Cl:55])=[CH:50][CH:51]=[CH:52][C:53]=1[Cl:54]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22507589Benzyl 2-methylpiperazine-1-carboxylateHCID 226481005-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-sulfonyl chloride

Product 1

HCID 22647988Benzyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]sulfonyl}-2-methylpiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl 2-methylpiperazine-1-carboxylate (34 mg, 0.144 mmol) and diisopropylethylamine (19 mg, 0.144 mmol) were added to a mixture of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-sulfonyl chloride (60 mg, 0.096 mmol) (COMPOUND CCC8) in 1 mL THF. The mixture was heated to 80° C. and stirred at this temperature for ca. 1 h. The reaction mixture was cooled to rt and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 50:50 hexanes-acetone to yield benzyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]sulfonyl}-2-methylpiperazine-1-carboxylate. Mass spectrum (ESI) 819.1 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated
  3. customThe residue was purified by preparative thin-layer chromatography
  4. washeluting with 50:50 hexanes-acetone

Sources & evidence

ORD record
ord-e4619375bc154bcbaa3f39a51cf3cddd
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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