Potassium Carbonate → HCID 57725678, compound

HRID 1922272Notes

Reaction equation

HRID 1922272 reaction equation
[F:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]2[S:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.Br[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[CH:16]1([CH2:15][NH:10][C:8]2[S:9][C:5]3[CH:4]=[C:3]([O:12][CH3:13])[C:2]([F:1])=[CH:11][C:6]=3[N:7]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 45076940HCID 45076940, compound

Product 1

HCID 57725678HCID 57725678, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To the solution of 5-fluoro-6-methoxybenzo[d]thiazol-2-amine (350 mg, 1.76 mmol, 1.0 eq) in 2 mL of NMP was added bromomethyl cyclohexane (370 μL, 2.65 mmol, 1.5 eq) and potassium carbonate (366 mg, 2.65 mmol, 1.5 eq) at room temperature. The reaction mixture was stirred at 80° C. for 24 hours with subsequent addition of reagents till reaction completion and thereafter quenched with saturated sodium bicarbonate solution (100 mL) which was then extracted with ethyl acetate (125 mL×3), combined organic layers dried over sodium sulfate, filtered and condensed under reduced pressure. Purification of the crude over ISCO using slow gradient of 0%-50% ethyl acetate-hexane gave 310 mg of product in 60% yield. LC/MS (m/z) [295.1] (MH+)

Workup

  1. customquenched with saturated sodium bicarbonate solution (100 mL) which
  2. extractionwas then extracted with ethyl acetate (125 mL×3)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customcondensed under reduced pressure
  6. customPurification of the crude over ISCO

Sources & evidence

ORD record
ord-fbc29f6d50aa40c4993b8d57aa098d50
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

Loading…