2-Amino-4-[2-(3-{[tert-butyl (dimethyl)silyl]oxy}prop-1-yn-1-yl)-1,3-thiazol-4-yl]-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)pyridine-3,5-dicarbonitrile → 2-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-[2-(3-hydroxypropyl)-1,3-thiazol-4-yl]pyridine-3,5-dicarbonitrile

HRID 1969494Notes

Reaction equation

HRID 1969494 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[N:11]=[C:12]([C:15]#[C:16][CH2:17][O:18][Si](C(C)(C)C)(C)C)[S:13][CH:14]=2)[C:5]([C:26]#[N:27])=[C:4]([S:28][CH2:29][C:30]2[N:31]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[S:33][CH:34]=2)[N:3]=1.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[N:11]=[C:12]([CH2:15][CH2:16][CH2:17][OH:18])[S:13][CH:14]=2)[C:5]([C:26]#[N:27])=[C:4]([S:28][CH2:29][C:30]2[N:31]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[S:33][CH:34]=2)[N:3]=1

Participants

5

Reactant 2

HCID 673501122-Amino-4-[2-(3-{[tert-butyl (dimethyl)silyl]oxy}prop-1-yn-1-yl)-1,3-thiazol-4-yl]-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)pyridine-3,5-dicarbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 668964572-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}sulfanyl)-4-[2-(3-hydroxypropyl)-1,3-thiazol-4-yl]pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under argon, 220 mg of the mixture from Example 22A were initially charged in 10 ml of ethyl acetate, 110 mg of palladium (10% on activated carbon) were added and the mixture was hydrogenated at atmospheric hydrogen pressure and room temperature overnight. The catalyst was filtered off through Celite, the filter cake was washed with ethyl acetate and the filtrate was concentrated. The residue was purified by preparative HPLC. This gave 31 mg (17% of theory) of the target compound.

Workup

  1. filtrationThe catalyst was filtered off through Celite
  2. washthe filter cake was washed with ethyl acetate
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-98af547800a946e29ad76d0dd8d13b10
Source dataset
uspto-grants-2013_04
Patent number
US08426602B2

Reaction notes

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