Triethylamine → 3-{[4-(Methylsulfonyl)piperazin-1-yl]carbonyl}cyclobutanone

HRID 1159402Notes

Reaction equation

HRID 1159402 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[O:28]=[C:29]1[CH2:32][CH:31]([C:33]([OH:35])=O)[CH2:30]1.[CH3:36][S:37]([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)(=[O:39])=[O:38].C(N(CC)CC)C>CN(C=O)C>[CH3:36][S:37]([N:40]1[CH2:45][CH2:44][N:43]([C:33]([CH:31]2[CH2:30][C:29](=[O:28])[CH2:32]2)=[O:35])[CH2:42][CH2:41]1)(=[O:39])=[O:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7091611-(Methylsulfonyl)piperazineHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 686193583-{[4-(Methylsulfonyl)piperazin-1-yl]carbonyl}cyclobutanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

BOP (4.43 g, 10 mmol) was poured some more to a solution of 3-oxo-cyclobutanecarboxylic acid (1.14 g, 10 mmol), intermediate 35, 1-(Methanesulphonyl)piperazine (1.64 g, 10 mmol), and triethylamine (4.1 mL, 30 mmol) in DMF (10 mL) in argon under stirring at 0° C. The mixture was stirred for 20 h, evaporated, and the residue was dried at 0.5 mmHg. The residue was subjected to chromatography on SiO2 (200 g, 40-63 μm, CHCl3/hexane 8:2, 9:1, 9.5:0.5→CHCl3→CHCl3/i-PrOH 99:1→95:5) to give the title compound as white crystals in 2.2 g yield. GCMS data: M+ 260 (Calculated for C10H16N2O4S 260.31), 93.5%, r.t. 14.64 min. 1H-NMR data (dmso-d6): 3.56-3.64 (m, 4H), 3.50 (ddd, 1H, J=7.1 Hz, J=9 Hz, J=15 Hz), 3.20-3.29 (m, 4H), 3.08-3.15 (m, 4H), 2.89 (s, 3H).

Workup

  1. stirringThe mixture was stirred for 20 h
  2. customevaporated
  3. customthe residue was dried at 0.5 mmHg

Sources & evidence

ORD record
ord-e0336226f7c94a5a8fafc02908868d01
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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