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

HRID 2379331Notes

Reaction equation

HRID 2379331 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.[CH3:40][S:41]([NH:44][C:45]([C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([N+:53]([O-])=O)[CH:48]=1)=[O:46])(=[O:43])=[O:42]>CN(C)C=O>[CH2:39]1[CH2:38][CH:7]([C:9]2([NH:20][C:21]([NH:53][C:49]3[CH:50]=[CH:51][CH:52]=[C:47]([C:45]([NH:44][S:41]([CH3:40])(=[O:43])=[O:42])=[O:46])[CH:48]=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

5

Reactant 3

HCID 8471TriethylamineHCID 196035271-(Methylsulphonylaminocarbonyl)-3-nitrobenzeneHCID 21480451HCID 21480451, compound

Product 1

HCID 57159294N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]N'-[3-(methylsulphonylaminocarbonyl)phenyl]ureaYield 48.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The rifle 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 (0.5 g, 1.2 mmol), triethylamine (0.16 ml, 1.2 mmol), dimethylformamide (10 ml) and 1-(methylsulphonylaminocarbonyl)-3-nitrobenzene (0.25 g, 1.2 mmol). After recrystallisation from ethanol, the compound (0.15 g, 26%) was afforded as a pale beige solid. mp 175° C (dec.). 1H NMR (360 MHz, D6 -DMSO) δ 0.88 (1H, m), 1.10-1.67 (7H, m), 1.72-1.81 (1H, m), 1.91 (1H, m), 2.95 (1H, m), 3.32 (3H, s), 3.34 (3H, s) 5.08 (1H, d, J=8.2 Hz), 7.37 (3H,m), 7.47 (1H, d, J=7.9 Hz), 7.56 (2H, m), 7.64 (1H, dd, J=7.0 and 7.0 Hz), 7.75 (1H, d, J=7.9 Hz), 7.91 (1H, s), 9.21 (1H, s), 12.07 (1H, brs).

Workup

  1. customThe rifle compound was prepared in the same way as
  2. customAfter recrystallisation from ethanol

Sources & evidence

ORD record
ord-e73dcc5b1abe4c4bad2f85e51d8d8deb
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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