Diisopropylethylamine → HCID 86686916, compound

HRID 2363872Notes

Reaction equation

HRID 2363872 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:30])[CH2:11][C:12]1[C:21]([CH3:22])=[C:20]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:29])[CH:18]=2)[CH:13]=1.C(N(CC)C(C)C)(C)C.[CH:40]1([S:45](Cl)(=[O:47])=[O:46])[CH2:44][CH2:43][CH2:42][CH2:41]1>C(Cl)Cl.O>[CH3:8][O:9][C:10](=[O:30])[CH2:11][C:12]1[C:21]([CH3:22])=[C:20]([CH:23]2[CH2:24][CH2:25][N:26]([S:45]([CH:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)(=[O:47])=[O:46])[CH2:27][CH2:28]2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:29])[CH:18]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 3717197Cyclopentanesulfonyl chlorideHCID 86686889HCID 86686889, compound

Product 1

HCID 86686916HCID 86686916, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (which may be prepared as described above; 102 mg, 0.237 mmol) and N,N-diisopropylethylamine (124 μL, 0.711 mmol) in methylene chloride (10.0 mL) was added cyclopentanesulfonyl chloride (62.5 μL, 0.474 mmol). The reaction mixture was stirred at 0° C. for 20 minutes, then it was warmed to room temperature and stirred at room temperature overnight. The reaction mixture was diluted with water (25 mL). The resulting mixture was extracted with methylene chloride (2×30 mL). The organic phase was dried over MgSO4, filtered, and concentrated. Silica gel chromatography (33% ethyl acetate in hexanes) provided [4-(1-cyclopentanesulfonyl-piperidin-4-yl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (64.8 mg, 61%). MS cald. For C24H31FNO4S [(M+H)+]: 448, obsd. 448.2.

Workup

  1. temperatureit was warmed to room temperature
  2. stirringstirred at room temperature overnight
  3. extractionThe resulting mixture was extracted with methylene chloride (2×30 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-916c7542291945a4b6a1c26fa759cae9
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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