HCID 70975098, compound → HCID 70974879, compound

HRID 409351Notes

Reaction equation

HRID 409351 reaction equation
Br[C:2]1([NH:7][CH2:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)([CH3:11])[CH3:10])[S:6][NH:5][CH:4]=[N:3]1.[C:19]([Cu])#[N:20]>>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]([CH3:11])([CH3:10])[CH2:8][NH:7][C:2]2[S:6][N:5]=[C:4]([C:19]#[N:20])[N:3]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 70975098HCID 70975098, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 70974879HCID 70974879, compoundYield 9%

Conditions

Temperature
120 °C

Procedure

5-Bromo-N-(2-(4-fluorophenyl)-2-methylpropyl)-1,2,4-thiadiazol-5-amine (635 mg, 1.92 mmol, 1.0 equiv) and CuCN (224 mg, 2.5 mmol, 1.3 equiv) were added to a microwave vial equipped with a stirbar. A septum was affixed to the vial, and the vial was purged with nitrogen for ˜5 min. DMF (2.5 mL) was then added, and the vial was sealed and heated for 20 min at 120° C. in a microwave. The reaction mixture was diluted with EtOAc and washed with sat'd. aq. NaHCO3 and brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. Purification by reverse phase HPLC provided the title compound (47 mg, 9%). m/z=275.0 [M−H]−.

Workup

  1. customvial equipped with a stirbar
  2. customwas purged with nitrogen for ˜5 min
  3. additionDMF (2.5 mL) was then added
  4. customthe vial was sealed
  5. additionThe reaction mixture was diluted with EtOAc
  6. washwashed with sat'd
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-881e3b85ed7e4238933d8cd8930f5116
Source dataset
uspto-grants-2014_06
Patent number
US08759380B2

Reaction notes

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