4,5-Dimethyl-1,3-thiazol-2-amine--hydrogen chloride (1/1) → HCID 58897150, compound

HRID 1993618Notes

Reaction equation

HRID 1993618 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([F:20])[CH:11]=2)=[NH:9])=[N:6][CH:7]=1.Cl.[CH3:22][C:23]1[N:24]=[C:25](N)[S:26][C:27]=1[CH3:28]>CC1C=CC=CC=1C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](/[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:13]=[C:12]([F:20])[CH:11]=2)=[N:9]/[C:25]2[S:26][C:27]([CH3:28])=[C:23]([CH3:22])[N:24]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 162113874,5-Dimethyl-1,3-thiazol-2-amine--hydrogen chloride (1/1)HCID 58897172HCID 58897172, compound

Product 1

HCID 58897150HCID 58897150, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of (5-chloropyridin-2-yl)(3-fluoro-5-(trifluoromethyl)phenyl)methanimine (1.7 g, 5.6 mmol) and 4,5-dimethylthiazol-2-amine HCl salt (900 mg, 5 mmol) in o-xylene (10 mL) was heated at 150° C. for 18 h, then allowed to cool to room temperature. The solvent was removed under reduced pressure and the residue purified by ISCO chromatography (80 g column) using hexanes/EtOAc (0-40%) over 25 min to give (E)-N-((5-chloropyridin-2-yl)(3-fluoro-5-(trifluoromethyl)phenyl)methylene)-4,5-dimethylthiazol-2-amine as a beige solid (910 mg, 44% yield). LCMS RT=4.00 min [M+H] 413.87 (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by ISCO chromatography (80 g column)
  3. customover 25 min

Sources & evidence

ORD record
ord-41d78d0e522c467490e8a66ac4adeba8
Source dataset
uspto-grants-2010_01
Patent number
US07652023B2

Reaction notes

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