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

HRID 2379342Notes

Reaction equation

HRID 2379342 reaction equation
C1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][CH2:19][CH3:20])[C:10](=[O:21])[CH:9]([NH:22][C:23]([O:25]C3C=CC([N+]([O-])=O)=CC=3)=O)[N:8]=2)CCCCC1.C(N([CH2:40][CH3:41])CC)C.CN(C)C=O.[CH3:47][S:48]([NH:51][C:52]([C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([NH2:60])[CH:55]=1)=[O:53])(=[O:50])=[O:49]>CO>[CH2:41]1[CH2:40][CH:7]([C:9]2([NH:22][C:23]([NH:60][C:56]3[CH:57]=[CH:58][CH:59]=[C:54]([C:52]([NH:51][S:48]([CH3:47])(=[O:50])=[O:49])=[O:53])[CH:55]=3)=[O:25])[N:8]=[CH:7][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][CH2:19][CH3:20])[C:10]2=[O:21])[CH2:13][CH2:12][CH2:17]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 212017011-(Methylsulphonylaminocarbonyl)-3-aminobenzeneHCID 214804635-cyclohexyl-1,3-dihydro-1-propyl-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one

Product 1

HCID 57319621N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-propyl-2-oxo-1H-1,4-benzodiazepin-3-yl]N'-[3-(methylsulphonylaminocarbonyl)phenyl]urea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared from 5-cyclohexyl-1,3-dihydro-1-propyl-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (0.3 g, 0.65 mmol), triethylamine (90 μl, 0.65 mmol), dimethylformamide (6 ml) and 1-(methylsulphonylaminocarbonyl)-3-aminobenzene ( 0.15 g, 7.1 mmol) [Example 16, Step 2] using the procedure described in Example 11, Step 4. The product (0.16 g, 46%) was afforded as a cream solid after trituration with hot methanol. mp 205° C. (dec.). 1H NMR (360 MHz, D6 -DMSO) δ 0.73 (3H, t, J=7.3 Hz), 0.86-1.00 (1H, m), 1.08-1.42 (5H, m), 1.43-1.54 (2H, m), 1.57-1.67 (2H, m), 1.74-1.83 (1H, m), 1.87-1.96 (1H, m), 2.91-3.01 (1H, m), 3.33 (3H, s), 3.62-3.72 (1H, m), 4.16-4.26 (1H, m), 5.04 (1H, d, J=7.8 Hz), 7.34-7.43 (3H, m), 7.47 (1H, d, 7.8 Hz), 7.56-7.68 (3H, m), 7.77 (1H, d, J=7.7 Hz), 7.91 (1H, dd, J=1.9 and 1.9 Hz), 9.20 (1H, s), 12.04 (1H, brs).

Sources & evidence

ORD record
ord-4c8fd076e29b4393b446139214e87aa8
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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