Dimethylformamide → N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl] N'-[3-(phenylcarbonylaminosulphonyl) phenyl]urea

HRID 2379324Notes

Reaction equation

HRID 2379324 reaction equation
C1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH3:18])[C:10](=[O:19])[CH:9]([NH:20][C:21]([O:23]C3C=CC([N+]([O-])=O)=CC=3)=O)[N:8]=2)CCCCC1.C(N([CH2:38][CH3:39])CC)C.CN(C)C=O.[C:45]1([C:51]([NH:53][S:54]([C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([NH2:63])[CH:58]=2)(=[O:56])=[O:55])=[O:52])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CO>[CH2:39]1[CH2:38][CH:7]([C:9]2([NH:20][C:21]([NH:63][C:59]3[CH:60]=[CH:61][CH:62]=[C:57]([S:54]([NH:53][C:51]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[O:52])(=[O:56])=[O:55])[CH:58]=3)=[O:23])[N:8]=[CH:7][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH3:18])[C:10]2=[O:19])[CH2:13][CH2:12][CH2:17]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 146178143-amino-N-benzoyl-benzenesulfonamideHCID 21480451HCID 21480451, compound

Product 1

HCID 131718765N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl] N'-[3-(phenylcarbonylaminosulphonyl) phenyl]urea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared in the same way as that described in Example 11, Step 4, using 5-cyclohexyl-1,3-dihydro-1-methyl-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiaZepin-2-one (0.3 g, 0.69 mmol), triethylamine (96 μl, 0.69 mmol), dimethylformamide (6 ml) and 1-(phenylcarbonylaminosulphonyl)-3-aminobenzene (0.21 g, 0.76 mmol). After trituration with methanol, the compound (0.16 g, 41%) was afforded as a colourless solid. mp 200°-202° C. 1H NMR (360 MHz, D6 -DMSO) δ 0.91 (1H, m), 1.10-1.40 (3H, m), 1.42-1.69 (4H, m), 1.78 (1H, m), 1.92 (1H, m), 2.94 (1H, m), 3.32 (3H, s), 5.06 (1H, d, J=8.1 Hz), 7.36 (2H, m), 7.45-7.56 (6H, m), 7.62 (2H, m); 7.75 (1H, d, J=7.9 Hz), 7.84 (2H, m), 8.17 (1H, s), 9.42 (1H, s), 12.50 (1H, brs).

Sources & evidence

ORD record
ord-6813b6495bd14af69f9687ca0ed79d70
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

Loading…