Pyridine → HCID 22041810, compound

HRID 990313Notes

Reaction equation

HRID 990313 reaction equation
[CH:1]1[C:13]2[CH:12]([O:14][C:15]([NH:17][C:18]3[CH:27]=[C:26]4[C:21]([CH:22]=[CH:23][C:24]([C:28](O)=[O:29])=[CH:25]4)=[CH:20][CH:19]=3)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.N1C=CC=CC=1.[NH2:41][C:42]1[CH:43]=[C:44]([S:48]([O:51][C:52]2[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=2)(=[O:50])=[O:49])[CH:45]=[CH:46][CH:47]=1>C(Cl)(Cl)Cl>[CH:10]1[C:11]2[CH:12]([O:14][C:15]([NH:17][C:18]3[CH:27]=[C:26]4[C:21]([CH:22]=[CH:23][C:24]([C:28]([NH:41][C:42]5[CH:43]=[C:44]([S:48]([O:51][C:52]6[CH:53]=[CH:54][C:55]([CH3:58])=[CH:56][CH:57]=6)(=[O:50])=[O:49])[CH:45]=[CH:46][CH:47]=5)=[O:29])=[CH:25]4)=[CH:20][CH:19]=3)=[O:16])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 24386Thionyl ChlorideHCID 11300023HCID 11300023, compound2×HCID 18421080HCID 18421080, compound

Product 1

HCID 22041810HCID 22041810, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 104 mg (0.026 mmol) of compound 107 was added 6.5 mL of chloroform, 1.3 mL of thionyl chloride, and 100 μL of pyridine. The reaction was allowed to stir at ambient temperature for 3 hours and then all volatiles were removed in vacuo. The residue was stripped in vacuo from chloroform twice. To the resulting solid, suspended in 15 mL of chloroform was added 74 mg (0.028 mmol) of 4-methylphenyl 3-aminobenzenesulfonate (compound 5) and 27 μL (0.033 mmol) of pyridine as a solution in 1.5 mL of chloroform. The reaction was allowed to stir at ambient temperature for 16 hours, after which it was partitioned between ethyl acetate and 1 N HCl (aqueous). The organic layer was dried (magnesium sulfate), filtered, and the volatiles were removed in vacuo. The resulting residue was treated with diethyl ether. and the solid precipitate collected by vacuum filtration. This provided 110 mg of compound 108.

Workup

  1. customall volatiles were removed in vacuo
  2. stirringto stir at ambient temperature for 16 hours
  3. customafter which it was partitioned between ethyl acetate and 1 N HCl (aqueous)
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. customthe volatiles were removed in vacuo
  7. additionThe resulting residue was treated with diethyl ether
  8. filtrationand the solid precipitate collected by vacuum filtration

Sources & evidence

ORD record
ord-ebb6f3ed5e4648018dd0ef6effe15c47
Source dataset
uspto-grants-2002_10
Patent number
US06458998B1

Reaction notes

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