Sodium Hydroxide → HCID 22953801, compound

HRID 861095Notes

Reaction equation

HRID 861095 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH3:35][O:36][CH2:37][CH2:38]Br.[OH-].[Na+]>CN(C=O)C>[CH3:35][O:36][CH2:37][CH2:38][N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 809722-Bromoethyl methyl etherHCID 81531DiisopropylethylamineHCID 22037252HCID 22037252, compound

Product 1

HCID 22953801HCID 22953801, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 5-(4-piperidyl)-4-(4-pyridyl)-3-(4-chlorophenyl)pyrazole hydrochloride (Example C-74) (500 mg, 1.2 mmol) in 12 mL of DMF was added Hunig's base (790 mg, 6.1 mmol) and 2-bromoethyl methyl ether (850 mg, 6.1 mmol). The solution was stirred at room temperature for 5 days. The solution was poured onto 2.5 N NaOH and was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water (3×100 mL) and brine (1×100 mL). The organic phase was dried over Na2SO4 and was filtered. The solvent was removed under reduced pressure to leave a solid. The solid was triturated and filtered to leave the title compound: 1HNMR (CDCl3) δ 8.63 (d, J=4.23 Hz, 2H), 7.28 (m, 4H), 7.14 (d, J=4.43 Hz, 2H), 3.57 (t, J=5.24 Hz, 2H), 3.38 (s, 3H), 3.14 (bd, J=10.1 Hz, 2H), 2.79 (m, 1H), 2.68 (t, J=5.04, 2H), 2.08 (m, 4H, 1.92 (m, 2H). MS (M+H): 397 (base peak).

Workup

  1. extractionwas extracted with ethyl acetate (3×100 mL)
  2. washThe combined extracts were washed with water (3×100 mL) and brine (1×100 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationwas filtered
  5. customThe solvent was removed under reduced pressure
  6. customto leave a solid
  7. customThe solid was triturated
  8. filtrationfiltered

Sources & evidence

ORD record
ord-4df3eb6e03a14ea494efbd57e4223f1e
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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