Triethylamine → HCID 131718766, compound

HRID 2379328Notes

Reaction equation

HRID 2379328 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]([NH:43][S:44]([C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([NH2:53])[CH:48]=1)(=[O:46])=[O:45])=[O:42]>CN(C)C=O>[CH2:39]1[CH2:38][CH:7]([C:9]2([NH:20][C:21]([NH:53][C:49]3[CH:50]=[CH:51][CH:52]=[C:47]([S:44]([NH:43][C:41]([CH3:40])=[O:42])(=[O:46])=[O:45])[CH:48]=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 504048N-(3-aminophenyl)sulfonylacetamideHCID 21480451HCID 21480451, compound

Product 1

HCID 131718766HCID 131718766, compoundYield 65.2%

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 (0.5 g, 1.2 mmol), triethylamine (0.16 ml, 1.2 mmol), dimethylformamide (10 ml) and 1-(methylcarbonylaminosulphonyl)-3-aminobenzene (0.26 g, 1.2 mmol).After recrystallisation from methanol, the title compound (0.2 g, 34%) was afforded as a colourless solid. mp 195°-198° C. 1H NMR (360 MHz, D6 -DMSO) δ 0.87-0.99 (1H, m), 1.10-1.66 (7H, m), 1.78 (1H, m), 1.94 (1H, m), 1.91 (3H, s), 2.95 (1H, m), 3.30 (3H, s), 5.07 (1H, d, J=8.3 Hz), 7.39 (4H, m), 7.54 (2H, m), 7.64 (1H, dd, J=7.9 and 7.9 Hz), 7.76 (1H, d, J=7.9 Hz), 8.07 (1H, s), 9.42 (1H, s), 11.99 (1H, brs).

Workup

  1. customThe title compound was prepared in the same way as
  2. custom.After recrystallisation from methanol

Sources & evidence

ORD record
ord-08acf4f698aa480ea785d9605a6f2bb4
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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