Water → HCID 69226320, compound

HRID 2220834Notes

Reaction equation

HRID 2220834 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8].I[CH2:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]([C:37]#[N:38])[C:28]=1[O:39][CH3:40].[H-].[Na+].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([N:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]2)[CH2:10][O:11][CH2:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[C:29]([C:37]#[N:38])[C:28]=2[O:39][CH3:40])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69225254HCID 69225254, compoundHCID 69226896HCID 69226896, compound

Product 1

HCID 69226320HCID 69226320, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The requisite tert-butyl 4-{1-(3-chloro-4-fluorophenyl)-2-[(3-cyano-2-methoxy-1-naphthyl)methoxy]ethyl}piperazine-1-carboxylate was synthesized using the following method. tert-Butyl 4-[1-(3-chloro-4-fluorophenyl)-2-hydroxyethyl]piperazine-1-carboxylate (65 mg, 0.18 mmol) was dissolved in THF (1.8 mL). 4-(Iodomethyl)-3-methoxy-2-naphthonitrile (70 mg, 0.22 mmol) was added followed by NaH (9 mg, 0.36 mmol). After reacting at RT overnight, water (60 mL) was added. The mixture was extracted with EtOAc (40 mL). The organic phase was dried over Na2SO4, filtered through a pad of diatomaceous earth and the volatiles removed under reduce pressure. Chromatography of the residue on SiO2 (0-30% EtOAc:hexane) afforded the title compound (99 mg). MS m/z 554.6 (M+H)+. The requisite tert-butyl 4-[1-(3-chloro-4-fluorophenyl)-2-hydroxyethyl]piperazine-1-carboxylate was synthesized using the following method.

Workup

  1. extractionThe mixture was extracted with EtOAc (40 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered through a pad of diatomaceous earth
  4. customthe volatiles removed

Sources & evidence

ORD record
ord-9369f7f2979b4bea94d7e5281fd6b0ee
Source dataset
uspto-grants-2008_05
Patent number
US07368448B2

Reaction notes

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