Sulfamide → [4-(1,1-Dioxo-1lambda6-[1,2,6]thiadiazinan-4-yl)-phenyl]-carbamic acid tert-butyl ester

HRID 2219616Notes

Reaction equation

HRID 2219616 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:17][NH2:18])[CH2:15][NH2:16])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[S:20](N)(N)(=[O:22])=[O:21]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:15][NH:16][S:20](=[O:22])(=[O:21])[NH:18][CH2:17]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 59771216[4-(2-Amino-1-aminomethyl-ethyl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 59771229[4-(1,1-Dioxo-1lambda6-[1,2,6]thiadiazinan-4-yl)-phenyl]-carbamic acid tert-butyl esterYield 64.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

[4-(2-Amino-1-aminomethyl-ethyl)-phenyl]-carbamic acid tert-butyl ester (as prepared in Example 4, step (b), 30.4 mg, 0.114 mmol) and sulfamide (15.4 mg, 0.802 mmol) in pyridine (0.7 mL) was heated at reflux for 4 h. The reaction mixture was concentrated in vacuo, and the residue was purified on silica (20%-70% EtOAc-hexane) to obtain the title compound (24 mg, 64%): 1H-NMR (DMSO-d6; 400 MHz): δ 9.35 (br s, 1H), 7.45 (m, 2H), 7.15 (m, 2H), 6.73 (m, 2H), 3.52 (m, 2H), 3.27 (m, 2H), 2.85 (m, 1H), 1.52 (s, 9H).

Workup

  1. temperatureat reflux for 4 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified on silica (20%-70% EtOAc-hexane)

Sources & evidence

ORD record
ord-a4a803c328c64564a8247ce88353bd2f
Source dataset
uspto-grants-2008_08
Patent number
US07414050B2

Reaction notes

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