2-Aminothiazole → HCID 56600789, compound

HRID 1619591Notes

Reaction equation

HRID 1619591 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:27](Cl)(=[O:29])=[O:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1.[NH2:31][C:32]1[S:33][CH:34]=[CH:35][N:36]=1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([S:27]([NH:31][C:32]2[S:33][CH:34]=[CH:35][N:36]=2)(=[O:29])=[O:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 58042351HCID 58042351, compound

Product 1

HCID 56600789HCID 56600789, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-fluoro-4-{[3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-yl]oxy}benzenesulfonyl chloride (Preparation 31, 350 mg, 0.79 mmol) and 2-amino thiazole (158 mg, 1.58 mmol) in pyridine (2 mL) was stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo and the residue acidified to pH 4-5 with a 1M aqueous solution of hydrogen chloride. The mixture was extraction with ethyl acetate (3×10 mL). The organic layer was separated and washed sequentially with water (3×5 mL) and brine (1×5 mL), then dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (100-200 mesh silica gel, 35% ethyl acetate in hexane) followed by trituration with pentane to afford the title compound as an off white solid (75 mg, 19%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextraction with ethyl acetate (3×10 mL)
  3. customThe organic layer was separated
  4. washwashed sequentially with water (3×5 mL) and brine (1×5 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (100-200 mesh silica gel, 35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-518f0c66022a4c1f85c0eea985d22207
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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