Dimethylformamide → HCID 131718769, compound

HRID 2379354Notes

Reaction equation

HRID 2379354 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.CN(C)C=O.[CH3:45][C:46]([CH3:61])([C:48]([NH:50][S:51]([C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([NH2:60])[CH:55]=1)(=[O:53])=[O:52])=[O:49])[CH3:47]>CO>[CH2:39]1[CH2:38][CH:7]([C:9]2([NH:20][C:21]([NH:60][C:56]3[CH:57]=[CH:58][CH:59]=[C:54]([S:51]([NH:50][C:48]([C:46]([CH3:61])([CH3:45])[CH3:47])=[O:49])(=[O:53])=[O:52])[CH:55]=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

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 18957772HCID 18957772, compoundHCID 21480451HCID 21480451, compound

Product 1

HCID 131718769HCID 131718769, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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-methyl3(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-dimethylethylcarbonylaminosulphonyl)-3-aminobenzene (194 mg, 0.76 mmol). After trituration with hot methanol, the title compound (0.15 g, 39%) was afforded as a colourless solid. mp 235° C. (dec.). 1H NMR (360 MHz, D6-DMSO) δ 3 0.84-0.98 (1H, m), 1.04(9H, s), 1.06-1.40 (4H, m), 1.41-1.68 (3H, m), 1.73-1.82 (1H, m), 1.88-1.96 (1H, m), 2.89-3.00 (1H, m), 3.33 (3H, s), 5.06 (1H, d, J=8.3 Hz), 7.32-7.50 (4H, m), 7.52-7.58 (2H, m), 7.64 (1H, t, J=7.0 Hz), 7.75 (1H, d, J=7.9 Hz), 8.03 (1H, s), 9.39 (1H, s), 11.62 (1H, brs).

Workup

  1. customThe title compound was prepared in the same way as

Sources & evidence

ORD record
ord-596c3da7dffc4caa9ccedd850b0d480f
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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