Hydrochloric Acid → 3-(Benzyloxy)-N-(4-methylthiazol-2-yl)-5-(1-phenylvinyl)pyridin-2-amine hydrochloride

HRID 1426159Notes

Reaction equation

HRID 1426159 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH3:22])[N:21]=2)=[N:11][CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]C.C([Li])CCC.[C:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)[CH3:31].[ClH:39].C(=O)(O)[O-].[Na+]>>[ClH:39].[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH3:22])[N:21]=2)=[N:11][CH:12]=[C:13]([C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH2:31])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 6

HCID 313Hydrochloric Acid2×HCID 7410AcetophenoneHCID 516892Sodium BicarbonateHCID 16061466HCID 16061466, compoundHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 866396973-(Benzyloxy)-N-(4-methylthiazol-2-yl)-5-(1-phenylvinyl)pyridin-2-amine hydrochlorideYield 47.1%

Procedure

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.250 g, 0.664 mmol), MeLi (0.519 ml, 0.831 mmol), butyllithium (0.332 ml, 0.831 mmol), and acetophenone (0.0798 g, 0.664 mmol) were reacted according to the method of Example 7. 1M HCl was added and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured onto ice and saturated sodium bicarbonate and extracted twice with dichloromethane. The organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography (5-10% EtOAc in hexane) to provide the title compound (0.125 g, 47.1% yield) after HCl salt formation. 1H NMR (DMSO-d6) δ 7.81 (d, 1H), 7.54 (m, 2H), 7.48 (m, 1H), 7.37 (m, 6H), 7.30 (m, 2H), 6.81 (s, 1H), 5.60 (s, 1H), 5.54 (s, 1H), 5.33 (s, 2H), 2.31 (s, 3H). Mass spectrum (apci) m/z=400.1 (M+H-HCl)

Workup

  1. extractionextracted twice with dichloromethane
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (5-10% EtOAc in hexane)

Sources & evidence

ORD record
ord-56e224aa634d4db1a538ea8b99dd439b
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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