Hydrochloric Acid → HCID 71544460, compound

HRID 2406494Notes

Reaction equation

HRID 2406494 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:13]([NH:21]C(=O)C)([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:13]([C:15]3[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=3)([NH2:21])[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71544570HCID 71544570, compound

Product 1

HCID 71544460HCID 71544460, compoundYield 55.7%

Procedure

A stirred solution of N-(1-(2-(4-fluorophenyl)thiazol-5-yl)-1-(pyridin-4-yl)ethyl)acetamide (Example 69) (0.04 g, 0.12 mmol) in concentrated HCl (0.07 mL, 3.03 mmol) was heated at 100° C. for 24 hrs in a sealed glass tube. The reaction mixture was then cooled to room temperature and neutralized with 10% NaOH solution (2 mL). The aqueous layer was extracted with ethyl acetate (3×100 mL), and the combined organic layers were concentrated under vacuum. The crude product residue obtained was purified by preparative TLC using eluting solvent as MeOH:CH2Cl2 (3:7) to afford 20 mg (38%) of 1-(2-(4-fluorophenyl)thiazol-5-yl)-1-(pyridin-4-yl)ethanamine as a colorless solid. 1H NMR (400 MHz, DMSO-d6): δ 8.50 (d, 2H, J=5.6 Hz), 7.91-7.88 (m, 2H), 7.70 (s, 1H), 7.51 (d, 2H, J=6.4 Hz), 7.28 (t, 2H, J=8.8 Hz), 2.81 (s, 2H); 1.85 (s, 3H); LC-MS m/z calculated for [M+H]+ 300.09, found 300.1.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  2. concentrationthe combined organic layers were concentrated under vacuum
  3. customThe crude product residue obtained
  4. customwas purified by preparative TLC
  5. washusing eluting solvent as MeOH:CH2Cl2 (3:7)

Sources & evidence

ORD record
ord-feb9f6f5b2f14389afb2663012b9816e
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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