Water → HCID 22272563, compound

HRID 230519Notes

Reaction equation

HRID 230519 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=1.[N:17]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[C:27]([O:26][C:24]([N:17]1[CH2:23][CH2:22][CH2:21][N:20]([C:2]2[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=2)[CH2:19][CH2:18]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 22272449HCID 22272449, compound

Product 1

HCID 22272563HCID 22272563, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-(5-Fluoro-2-nitrophenyl)-N-methylmethanesulfonamide (3.1 g, 12.5 mmol), tert-butyl 1-homopiperazinecarboxylate (2.5 g) and potassium carbonate (2 g) were heated together in DMSO (50 mL) at 80° C. overnight. 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. Yield 4.6 g (86%); 1H NMR (400 MHz, CDCl3) δ 1.41 (s, 9 H), 2.0 (br s, 2 H), 3.01 (s, 3 H), 3.28 (s, 3 H), 3.3-3.8 (br, 8 H), 6.64 (d, J=8.1 Hz, 1 H), 6.74 (d, J=4.8 Hz, 1 H), 8.09 (d, J=8.1 Hz, 1 H); MS (ESI+) for C18H28N4O6S m/z 428.1709 (M+) (calc. 428.1730).

Workup

  1. temperatureto cool
  2. filtrationThe solid product was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-81d9b3aad4584435a95582d99b6602d2
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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