Water → tert-Butyl 4-{3-[ethyl(methylsulfonyl)amino]-4-nitrophenyl}-1,4-diazepane-1-carboxylate

HRID 230517Notes

Reaction equation

HRID 230517 reaction equation
[CH2:1]([N:3]([C:8]1[CH:13]=[C:12](F)[CH:11]=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16])[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2].[N:18]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH2:1]([N:3]([S:4]([CH3:7])(=[O:6])=[O:5])[C:8]1[CH:13]=[C:12]([N:21]2[CH2:22][CH2:23][CH2:24][N:18]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH2:20]2)[CH:11]=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 22272466N-ethyl-N-(5-fluoro-2-nitrophenyl)methanesulfonamide

Product 1

HCID 22272556tert-Butyl 4-{3-[ethyl(methylsulfonyl)amino]-4-nitrophenyl}-1,4-diazepane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-Ethyl-N-(5-fluoro-2-nitrophenyl)methanesulfonamide (3.2 g, 12.2 mmol), tert-butyl 1-homopiperazinecarboxylate (2.5 g) and potassium carbonate (2 g) were heated together in DMSO at 50° C. for 5 hours. The solution was allowed to cool and poured into 500 mL of water. The solid product was collected by filtration, washed with water and dried. The product was purified by flash chromatography (ethyl acetate:petrol 1:1). Yield 2.6 g (48%) 1H NMR (400 MHz, CDCl3) δ 1.16 (t, J=7.33 Hz, 3 H), 1.39 (s, 9 H), 2.0 (br, 2 H), 2.99 (s, 3 H), 3.2 (br, 2 H), 3.54-3.75 (br, 8 H), 6.65 (br d, J=9.3 Hz, 1 H), 6.67 (d, J=2.93 Hz, 1 H), 8.1 (d, J=9.3 Hz, 1 H); MS (ESI+) for C19H30N4O6S m/z 442 (M+).

Workup

  1. temperatureto cool
  2. filtrationThe solid product was collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe product was purified by flash chromatography (ethyl acetate:petrol 1:1)

Sources & evidence

ORD record
ord-384f4fd355d24922b0bf90830373bf26
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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