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

HRID 2379321Notes

Reaction equation

HRID 2379321 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.[CH:40]([S:43]([NH:46][C:47]([C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([NH2:55])[CH:50]=1)=[O:48])(=[O:45])=[O:44])([CH3:42])[CH3:41]>CN(C)C=O>[CH2:39]1[CH2:38][CH:7]([C:9]2([NH:20][C:21]([NH:55][C:51]3[CH:52]=[CH:53][CH:54]=[C:49]([C:47]([NH:46][S:43]([CH:40]([CH3:42])[CH3:41])(=[O:45])=[O:44])=[O:48])[CH:50]=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 189577783-Amino-N-(isopropylsulfonyl)benzamideHCID 21480451HCID 21480451, compound

Product 1

HCID 57012019N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl] N'-[3(isopropylsulphonylaminocarbonyl)phenyl]urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in the same way as that described in Example 11, Step 4, using 5-cyclohexyl-l,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-(isopropylsulphonylaminocarbonyl)-3-aminobenzene (0.175 mg, 0.72 mmol). After recrystallisation from ethanol the title compound (0.24 g, 65%) was afforded as a colourless solid. mp 165° C. (dec.). 1H NMR (360 MHz, D6 -DMSO) δ 0.87-0.98 (1H, m), 1.10-1.64 (7H, m), 1.30 (6H, d, J=6.9 Hz), 1.79 (1H, m), 1.88-1.96 (1H, m), 2.95 (1H, m), 3.33 (3H, s), 3.79 (1H, septet, J=6.9 Hz), 5.07 (1H, d, J=8.2 Hz), 7.37 (3H, m), 7.46 (1H, d, J=7.8 Hz), 7.55 (2H, m), 7.64 (1H, dd, J=7.1 and 7.1 Hz), 7.75 (1H, d, J=7.9 Hz), 7.92 (1H,s), 9.22 (1H,s), 11.93 (1H, brs).

Workup

  1. customAfter recrystallisation from ethanol the title compound (0.24 g, 65%)
  2. customwas afforded as a colourless solid

Sources & evidence

ORD record
ord-cee904e38c274ac486f88483e526faf6
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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