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

HRID 2379351Notes

Reaction equation

HRID 2379351 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][C:41]([CH3:56])([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]>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]([C:41]([CH3:56])([CH3:40])[CH3:42])(=[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 189577571-(1,1-Dimethylethylsulphonylaminocarbonyl)-3-aminobenzeneHCID 21480451HCID 21480451, compound

Product 1

HCID 57182989N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]N'-[3-(1,1-dimethylethylsulphonylaminocarbonyl)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-1,3-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-(1,1-dimethylethylsulphonylaminocarbonyl)-3-aminobenzene (0.19 g, 0.76 mmol). The product (176 mg, 46%) was afforded as a colourless solid after recrystallisation from ethanol. mp 180° C. (dec.). 1H NMR (360 MHz, D6-DMSO) δ 0.84-0.98 (1H, m), 1.38 (9H, s), 1.08-1.65 (7H, m), 1.71-1.81 (1H, m), 1.86-1.94 (1H, m), 2.88-2.98 (1H, m), 3.32 (3H, s), 5.08 (1H, d, J=8.3 Hz), 7.29-7.42 (4H, m), 7.54 (1H, s), 7.56 (1H, s), 7.64 (1H, t, J=7.7 Hz), 7.75 (1H, d, J= 7.9 Hz), 7.84 (1H, s), 9.19 (1H, s), 11.51 (1H, brs).

Sources & evidence

ORD record
ord-d2d8d28f6ca2408b975b6b643e0752e7
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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