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

HRID 2379340Notes

Reaction equation

HRID 2379340 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.[CH2:45]([S:47]([NH:50][C:51]([C:53]1[CH:58]=[CH:57][CH:56]=[C:55]([N+:59]([O-])=O)[CH:54]=1)=[O:52])(=[O:49])=[O:48])[CH3:46]>CO>[CH2:39]1[CH2:38][CH:7]([C:9]2([NH:20][C:21]([NH:59][C:55]3[CH:56]=[CH:57][CH:58]=[C:53]([C:51]([NH:50][S:47]([CH2:45][CH3:46])(=[O:49])=[O:48])=[O:52])[CH:54]=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 189577921-(Ethylsulphonylaminocarbonyl)-3-nitrobenzeneHCID 21480451HCID 21480451, compound

Product 1

HCID 57208594N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl] N'-[3-(ethylsulphonylaminocarbonyl)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)-[(4nitrophenyloxycarbonyl)amino]-2H- 1,4-benzodiazepin-2-one (0.25 g, 0.57 mmol), triethylamine (80 μl, 0.57 mmol), dimethylformamide (5ml) and 1-(ethylsulphonylaminocarbonyl)-3-nitrobenzene (0.14 g, 0.63 mmol). After trituration with hot methanol, the compound (125 mg, 42%) was afforded as a colourless solid. mp 210° C. (dec.). 1H NMR (360 MHz, D6 -DMSO) δ 0.86-0.98 (1H, m), 1.10-1.25 (2H, m), 1.23 (3H, t, J=7.4 Hz), 1.26-1.64 (5H, m), 1.72-1.80 (1H, m), 1.87-1.96 (1H, m), 2.88-2.99 (1H, m), 3.33 (3H, s), 3.48 (2H, q, J=7.4 Hz), 5.08 (1H, d, J=8.3 Hz), 7.31-7.42 (3H, m), 7.47 (1H, d, J=7.9 Hz), 7.52-7.58 (2H, m), 7.67 (1H, dd, J=7.9 and 7.8 Hz), 8.76-8.80 (1H, m), 7.92 (1H, dd, J=1.8 and 1.8 Hz), 9.21 (1H, s), 11.98 (1H, brs).

Sources & evidence

ORD record
ord-4fcb40a218ac4692ad804e0ba5dc63d0
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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