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

HRID 2379333Notes

Reaction equation

HRID 2379333 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.[F:40][C:41]([F:56])([F:55])[C:42]([NH:44][S:45]([C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([NH2:54])[CH:49]=1)(=[O:47])=[O:46])=[O:43]>CN(C)C=O>[CH2:39]1[CH2:38][CH:7]([C:9]2([NH:20][C:21]([NH:54][C:50]3[CH:51]=[CH:52][CH:53]=[C:48]([S:45]([NH:44][C:42]([C:41]([F:40])([F:55])[F:56])=[O:43])(=[O:46])=[O:47])[CH:49]=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 21480451HCID 21480451, compoundHCID 217455061-(Trifiuoromethyl carbonylaminosulphonyl)-3-aminobenzene

Product 1

HCID 131718767N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl] N'-[3-(trifiuoromethylcarbonylaminosulphonyl) phenyl]ureaYield 17.7%

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 (0.5 g, 1.2 mmol), triethylamine (0.16 ml, 1.2 mmol), dimethylformamide (10 ml) and 1-(trifiuoromethyl carbonylaminosulphonyl)-3-aminobenzene (0.32 g, 1.2 mmol). The product was purified by chromatography on silica gel eluting with dichloromethane-methanol (9:1). This afforded the title compound (60 mg, 9%) as a pale beige solid. mp 190° C. (dec.). 1H NMR (360 MHz, D6 -DMSO) δ 0.86-1.00 (1H, m), 1.10-1.67 (7H,m), 1.76 (1H, m), 1.89-1.98 (1H, m), 2.95 (1H, m), 3.33 (3H, s) 5.08 (1H, m), 7.28 (3H, m), 7.38 (1H, m), 7.52 ( 2H, m), 7.64 (1H, m), 7.77 (2H, m), 9.21 (1H,s).

Workup

  1. customThe title compound was prepared in the same way as
  2. customThe product was purified by chromatography on silica gel eluting with dichloromethane-methanol (9:1)

Sources & evidence

ORD record
ord-d9f62c39dcbe4fa59139b63cab4b1bd9
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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