4-Toluenesulfonyl chloride → HCID 86729592, compound

HRID 574204Notes

Reaction equation

HRID 574204 reaction equation
[NH2:1][C:2]1[C:3]([C:16]([NH:18][NH:19][C:20](=[O:35])[C:21]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH3:26])[C:22]([F:25])([F:24])[F:23])=O)=[N:4][C:5]([C:12]([F:15])([F:14])[F:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.C(N(CC)CC)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C(Cl)Cl>[CH2:28]([O:27][C:21]([C:20]1[O:35][C:16]([C:3]2[C:2]([NH2:1])=[N:7][C:6]([C:8]([F:9])([F:10])[F:11])=[C:5]([C:12]([F:13])([F:14])[F:15])[N:4]=2)=[N:18][N:19]=1)([CH3:26])[C:22]([F:25])([F:24])[F:23])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86729593HCID 86729593, compound

Product 1

HCID 86729592HCID 86729592, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3-amino-W-(2-(benzyloxy)-3,3,3-trifluoro-2-methylpropanoyl)-5,6-bis(trifluoromethyl)pyrazine-2-carbohydrazide (step 1) (510 mg, 0.982 mmol) in DCM (20 ml) was treated with triethylamine (0.411 ml, 2.95 mmol) and stirred at RT. Tosyl chloride (562 mg, 2.95 mmol) was added and stirring continued for 30 minutes. The reaction mixture was partitioned between EtOAc (50 ml) and 1M HCl (50 ml), shaken and separated. The organic portion was washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo to give a yellow oil. The crude product was purified by mass directed LC-MS eluting with MeCN/Water/0.1% TFA. The clean fractions were poured into EtOAc (50 ml) and washed with saturated NaHCO3 (50 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound as a white crystalline solid.

Workup

  1. stirringstirring
  2. customThe reaction mixture was partitioned between EtOAc (50 ml) and 1M HCl (50 ml)
  3. stirringshaken
  4. customseparated
  5. washThe organic portion was washed with brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil
  9. customThe crude product was purified by mass
  10. washeluting with MeCN/Water/0.1% TFA
  11. additionThe clean fractions were poured into EtOAc (50 ml)
  12. washwashed with saturated NaHCO3 (50 ml)
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9827bc023a04159a3f247131063b9c6
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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