Butylamine → HCID 18767793, compound

HRID 2300217Notes

Reaction equation

HRID 2300217 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:8]1[CH2:11][N:10]([S:12]([C:15]2[CH:20]=[CH:19][C:18](F)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:30]([NH2:34])[CH2:31][CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)N(C)CCC1.O>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:8]1[CH2:11][N:10]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:34][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 11430Potassium CarbonateHCID 18767769HCID 18767769, compound

Product 1

HCID 18767793HCID 18767793, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of Benzyl-[1-(4-fluoro-benzenesulfonyl)-azetidin-3-yl]-carbamicacid tert-butyl ester (0.21 g, 0.5 mmol) in N,N′-dimethylpropyleneurea (0.5 ml) was added butylamine (0.15 g, 2 mmol) and potassium carbonate (0.07 g, 0.5 mmol), and the mixture was stirred at 50° C. for 2 days. It was then cooled to room temperature and diluted with water (20 ml). The aqueous phase was removed, and the residue dissolved in ether (20 ml). The ether solution was washed with 0.5 N HCl, saturated sodium bicarbonate solution, and brine, and dried over anhydrous sodium sulfate. It was then filtered through a pad of silica gel. The filtrate was evaporated, and the residue was triturated with hexanes to give 0.23 g of a white solid; m.p. 115-116° C.; MS (ES) m/z 474.1 (MH+); HRMS (El) Calcd. for C25H35N3O4S (M+): 473.2348, Found: 473.2338.

Workup

  1. temperatureIt was then cooled to room temperature
  2. customThe aqueous phase was removed
  3. dissolutionthe residue dissolved in ether (20 ml)
  4. washThe ether solution was washed with 0.5 N HCl, saturated sodium bicarbonate solution, and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationIt was then filtered through a pad of silica gel
  7. customThe filtrate was evaporated
  8. customthe residue was triturated with hexanes

Sources & evidence

ORD record
ord-fcfd9736bdd346d9b0e33fd96a47cffa
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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