Hydrochloric Acid → 1-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanone hydrochloride

HRID 1426104Notes

Reaction equation

HRID 1426104 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:22]([OH:24])[CH3:23])[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+].[ClH:49]>ClCCl.CCOCC>[ClH:49].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:22](=[O:24])[CH3:23])[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 592256651-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanol

Product 1

HCID 866396581-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanone hydrochlorideYield 48.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent3×

Procedure

1-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanol (prepared according to Example 19; 0.128 g, 0.375 mmol) was placed in dichloromethane (5 mL). A solution of Dess-Martin periodinane (0.167 g, 0.394 mmol) in dichloromethane (7 mL) was added and the reaction mixture was stirred at room temperature for 20 minutes. 1M NaOH and ether were added, and the layers were separated. The organic layer was washed with 1M NaOH and water, then dried, filtered, and concentrated. The residue was purified by silica gel to provide the free base, which was dissolved in dichloromethane. 2M HCl was added and the solution was concentrated to afford 1-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanone hydrochloride (0.068 g, 48.3% yield). 1H NMR (DMSO-d6) δ 8.62 (d, 1H), 7.73 (m, 1H), 7.60 (m, 2H), 7.42 (m, 2H), 7.35 (m, 1H), 6.79 (s, 1H), 5.36 (s, 2H), 2.57 (s, 3H), 2.30 (s, 3H). Mass spectrum (apci) m/z=340.1 (M+H-HCl).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with 1M NaOH and water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel
  7. customto provide the free base, which
  8. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-6f9669e40e3b402090f5ab61122c7cf7
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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