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

HRID 2379335Notes

Reaction equation

HRID 2379335 reaction equation
C1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:10](=[O:22])[CH:9]([NH:23][C:24]([O:26]C3C=CC([N+]([O-])=O)=CC=3)=O)[N:8]=2)CCCCC1.C(N([CH2:41][CH3:42])CC)C.CN(C)C=O.[CH3:48][S:49]([NH:52][C:53]([C:55]1[CH:60]=[CH:59][CH:58]=[C:57]([NH2:61])[CH:56]=1)=[O:54])(=[O:51])=[O:50]>CO>[CH2:42]1[CH2:41][CH:7]([C:9]2([NH:23][C:24]([NH:61][C:57]3[CH:58]=[CH:59][CH:60]=[C:55]([C:53]([NH:52][S:49]([CH3:48])(=[O:51])=[O:50])=[O:54])[CH:56]=3)=[O:26])[N:8]=[CH:7][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:10]2=[O:22])[CH2:13][CH2:12][CH2:17]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 189577885-cyclohexyl-1,3-dihydro-l-(2-methylpropyl)-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-oneHCID 212017011-(Methylsulphonylaminocarbonyl)-3-aminobenzene

Product 1

HCID 57228583N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-(2-methylpropyl)-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-l-(2-methylpropyl)-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H- 1,4-benzodiazepin-2-one (0.3 g, 0.63 mmol), triethylamine (87 μl, 0.63 mmol), dimethylformamide (6 ml) and 1-(methylsulphonylaminocarbonyl)-3-aminobenzene (0.15 g, 0.69 mmol) [Example 16, Step 2] using the procedure described in Example 11, Step 4. The product (0.17 g, 49%) was afforded as a pale cream solid after trituration with methanol. mp 250°-252° C. 1H NMR (360 MHz, D6 -DMSO) δ 0.64 (3H, d, J=6.6 Hz), 0.76 (3H, d, J=6.7 Hz), 0.92-1.70 (9H, m), 1.74-1.82 (1H, m), 1.98 (1H, m), 2.90-3.30 (1H, m), 3.33 (3H, m), 3.62 (1H, dd, J=14.0 and 4.7 Hz), 4.14 (1H, dd, J=13.9 and. 9.4 Hz), 5.04 (1H, m), 7.37 (3H, m), 7.47 (1H, m), 7.60 (3H, m) , 7.78 (1H, m), 7.90 (1H, s), 9.18 (1H, s), 12.06 (1H, brs).

Sources & evidence

ORD record
ord-16658ead91ba4fe9889a5f72ba282485
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

Loading…