2-Aminothiazole → HCID 25138300, compound

HRID 533350Notes

Reaction equation

HRID 533350 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:5][CH:4]=1.[NH2:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1>N1C=CC=CC=1>[S:28]1[CH:29]=[CH:30][N:31]=[C:27]1[NH:26][S:20]([C:17]1[CH:18]=[CH:19][C:14]([S:11]([CH2:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:25])([F:24])[F:1])=[CH:4][CH:5]=2)(=[O:13])=[O:12])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 59544867HCID 59544867, compound

Product 1

HCID 25138300HCID 25138300, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4-[2-(4-Trifluoromethyl-phenyl)-ethanesulfonyl]-benzenesulfonyl chloride (1288 mg, 0.003120 mol) and 2-aminothiazole (0.31 g, 0.0031 mol) was added pyridine (20 mL). After stirring overnight, the reaction mixture was concentrated, dissolved in DMSO (4 mL) and purified by reversed phase chromatography (Phenomenex 250×30 mm 15 micron C18 column. 40 mL/min. Gradient 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA). The compound was further purified on silica gel (CHCl3-10% MeOH in CHCl3) to give 94 mg of a light brown solid. LCMS: M+477.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutiondissolved in DMSO (4 mL)
  3. custompurified by reversed phase chromatography (Phenomenex 250×30 mm 15 micron C18 column. 40 mL/min. Gradient 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA)
  4. customThe compound was further purified on silica gel (CHCl3-10% MeOH in CHCl3)

Sources & evidence

ORD record
ord-43073041b9bd43fda5f72e3d79bfdec1
Source dataset
uspto-grants-2014_10
Patent number
US08853250B2

Reaction notes

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