Potassium Carbonate → HCID 66652280, compound

HRID 2363074Notes

Reaction equation

HRID 2363074 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[F:35][C:36]1[CH:41]=[CH:40][C:39]([C:42](=[O:47])[CH2:43][CH2:44][CH2:45]I)=[CH:38][CH:37]=1>CN(C)C=O.C(OCC)(=O)C>[F:35][C:36]1[CH:37]=[CH:38][C:39]([C:42](=[O:47])[CH2:43][CH2:44][CH2:45][N:9]2[CH2:10][CH2:11][C:6]3([N:5]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:4][N:3]([C:18]4[CH:19]=[CH:20][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:22][CH:23]=4)[C:2]3=[O:1])[CH2:7][CH2:8]2)=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 30162324'-Fluoro-4-iodobutyrophenoneHCID 66652365HCID 66652365, compound

Product 1

HCID 66652280HCID 66652280, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of N-(4-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)phenyl)methanesulfonamide (0.2 g, 0.46 mmol) and potassium carbonate (0.191 g, 1.38 mmol) in N,N-dimethylformamide (5 mL), was added 1-(4-fluorophenyl)-4-iodobutan-1-one (0.134 g, 0.46 mmol). After stirring at 65° C. for 18 hours, the reaction mixture was diluted with ethyl acetate (25 mL), washed with water and brine. The organic phase was dried over MgSO4, filtered, concentrated and isolated by pTLC (10% methanol/dichloromethane) to obtain the product (0.03 g, 12%); 1H NMR (DMSO-d6): δ 1.70-1.90 (m, 4H), 2.40-2.49 (m, 2H), 2.66-2.84 (m, 6H), 2.97 (s, 3H), 3.05 (br, 2H), 5.12 (s, 2H), 6.88 (t, 1H, J=7.6 Hz) 6.99-7.03 (m, 2H), 7.26 (d, 4H, J=9.2 Hz), 7.34 (t, 2H, J=8.4 Hz), 7.76 (d, 2H, J=8.8 Hz), 8.04-8.07 (m, 2H), 9.73 (s, 1H); MS for C30H33FN4O4S m/z 565.3 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customisolated by pTLC (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7107090a5fa944189c190075e78fbcc9
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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