Diisopropylethylamine → HCID 86686917, compound

HRID 2363874Notes

Reaction equation

HRID 2363874 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.[N:40]1([S:45](Cl)(=[O:47])=[O:46])[CH2:44][CH2:43][CH2:42][CH2:41]1>C(Cl)Cl>[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]([N: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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 64839021-Pyrrolidinesulfonyl chlorideHCID 86686889HCID 86686889, compound

Product 1

HCID 86686917HCID 86686917, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 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 pyrrolidine-1-sulfonyl chloride (80.4 mg, 0.474 mmol). The reaction mixture was stirred at 0° C. for 25 minutes, and then warmed to room temperature and stirred overnight. During this time period the solvent evaporated to dryness. Additional methylene chloride (10 mL) was added in the morning. The reaction mixture was diluted with water (25 mL). The resulting mixture was extracted with ethyl acetate (2×30 mL). The organic phase was dried over MgSO4, filtered, and concentrated. Silica gel chromatography (33% ethyl acetate in hexanes) provided {6-fluoro-3-methyl-4-[1-(pyrrolidine-1-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (86.5 mg, 81%). MS cald. for C23H30FN2O4S [(M+H)+]: 449, obsd. 449.2.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. customDuring this time period the solvent evaporated to dryness
  4. additionAdditional methylene chloride (10 mL) was added in the morning
  5. additionThe reaction mixture was diluted with water (25 mL)
  6. extractionThe resulting mixture was extracted with ethyl acetate (2×30 mL)
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b8f99eda7ba94162a366a4ef809938d9
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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