2-Bromothiazole → HCID 71668250, compound

HRID 1507440Notes

Reaction equation

HRID 1507440 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([CH3:19])=[C:8]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:9]2)=[CH:4][CH:3]=1.Br[C:22]1[S:23][CH:24]=[CH:25][N:26]=1.N12CCCN=C1CCCCC2>CN1CCCC1=O>[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([CH3:19])=[C:8]([CH:13]3[CH2:18][CH2:17][N:16]([C:22]4[S:23][CH:24]=[CH:25][N:26]=4)[CH2:15][CH2:14]3)[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 764302-BromothiazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 117701633HCID 117701633, compound

Product 1

HCID 71668250HCID 71668250, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A solution of 7-hydroxy-3,8-dimethyl-2-(piperidin-4-yl)-4H-chromen-4-one (68 mg, 0.25 mmol) obtained in Example 7-2, 2-bromothiazole (45 μL, 0.28 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (56 μL, 0.38 mmol) in N-methylpyrrolidone (0.2 mL) was heated with stirring at 140° C. for 12 hours. The reaction solution was allowed to cool and then purified by silica gel column chromatography (chloroform/methanol=100/0→95/5) to obtain 24 mg of the title compound (yield: 27%).

Workup

  1. temperatureto cool
  2. custompurified by silica gel column chromatography (chloroform/methanol=100/0→95/5)

Sources & evidence

ORD record
ord-c9680c9323884a1a943bf5e53a91cb7b
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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