Pyridinium chloride → 3-cyano-2-[(2-{[(2S)-2-(3,4-Dichlorophenyl)pent-4-enyl]amino}ethyl)thio]-1-naphthoic acid

HRID 1767456Notes

Reaction equation

HRID 1767456 reaction equation
Cl.[C:2]([C:4]1[C:5]([S:18][CH2:19][CH2:20][NH:21][CH2:22][C@H:23]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:24][CH:25]=[CH2:26])=[C:6]([C:14]([O:16]C)=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)#[N:3].Cl.N1C=CC=CC=1>>[C:2]([C:4]1[C:5]([S:18][CH2:19][CH2:20][NH:21][CH2:22][C@H:23]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:24][CH:25]=[CH2:26])=[C:6]([C:14]([OH:16])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)#[N:3]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 69138873Methyl 3-Cyano-2-[(2-{[(2S)-2-(3,4-dichlorophenyl)pent-4-enyl]amino}ethyl)thio]-1-naphthoate Hydrochloride2×

Product 1

HCID 599794983-cyano-2-[(2-{[(2S)-2-(3,4-Dichlorophenyl)pent-4-enyl]amino}ethyl)thio]-1-naphthoic acidYield 100%

Conditions

Temperature
180 °C

Procedure

An evenly distributed mixture of methyl 3-cyano-2-[(2-{[(2S)-2-(3,4-dichlorophenyl)pent-4-enyl]amino}ethyl)thio]-1-naphthoate hydrochloride (Intermediate 5, 150 mg, 0.28 mmol) and pyridine hydrochloride (487 mg, 4.20 mmol) was heated at 180° C. for 5 min, cooled, and partitioned between ethyl acetate and water. The organic layer was washed with 1 N HCl and brine, dried (Na2SO4), and evaporated to dryness to give 135 mg (100% yield) of the title compound which was used without further purification.

Workup

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with 1 N HCl and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9dcccd2714f1448aa9a61fa30b587608
Source dataset
uspto-grants-2007_06
Patent number
US07235541B2

Reaction notes

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