Pyridine → HCID 68681999, compound

HRID 2234984Notes

Reaction equation

HRID 2234984 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:14]=[C:13](N)[C:12]([O:16][CH3:17])=[CH:11][CH:10]=2)[CH2:3]1.N1C=CC=CC=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[C:27]([F:35])[CH:26]=1>C(Cl)Cl>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([C:13]2[N:14]=[C:9]([N:4]3[CH2:3][C@H:2]([CH3:1])[NH:7][C@H:6]([CH3:8])[CH2:5]3)[CH:10]=[CH:11][C:12]=2[O:16][CH3:17])(=[O:32])=[O:33])=[C:27]([F:35])[CH:26]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27363104-Bromo-2-fluorobenzene-1-sulfonyl chlorideHCID 58988130HCID 58988130, compound

Product 1

HCID 68681999HCID 68681999, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-[(3R,5S)-3,5-Dimethyl-1-piperazinyl]-3-(methyloxy)-2-pyridinamine (D7, Method D) (2.25 mmol) was dissolved in DCM (5 mL) and pyridine (5 mL) and then cooled to 0° C. 4-Bromo-2-fluoro benzenesulfonyl chloride (0.738 g, 2.706 mmol), dissolved in DCM (5 mL) was then added dropwise and the reaction then allowed to warm to rt overnight. The reaction was then evaporated to a minimum and redissolved in DCM (100 mL) and washed with water (2×75 mL), saturated sodium hydrogen carbonate (3×75 mL) and brine (75 mL). The organic layer was dried (MgSO4) and evaporated to give a brown oil which was triturated with methanol and dried at 50° C. under high vac to give the title compound as a pale brown powder (D18) (0.400 g). MS (ES+) m/e 473/475 [M+H]+.

Workup

  1. additionwas then added dropwise
  2. customthe reaction
  3. customThe reaction was then evaporated to a minimum
  4. dissolutionredissolved in DCM (100 mL)
  5. washwashed with water (2×75 mL), saturated sodium hydrogen carbonate (3×75 mL) and brine (75 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated
  8. customto give a brown oil which
  9. customwas triturated with methanol
  10. customdried at 50° C. under high vac

Sources & evidence

ORD record
ord-d7df2eebecd34a919d8b762be15a45ff
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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