Pyridine → HCID 57852682, compound

HRID 1890151Notes

Reaction equation

HRID 1890151 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:19][CH2:20][OH:21])[C:10]=2[C:9]2[CH:22]=[CH:23][CH:24]=[CH:25][C:8]=2[S:7]1)=[O:5])[CH3:2].[C:28]1(C)[C:29]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:31]=[CH:32][CH:33]=1.N1C=CC=C[CH:40]=1>ClCCl>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:19][CH2:20][O:21][S:34]([C:29]3[CH:28]=[CH:33][C:32]([CH3:40])=[CH:31][CH:30]=3)(=[O:35])=[O:36])[C:10]=2[C:9]2[CH:22]=[CH:23][CH:24]=[CH:25][C:8]=2[S:7]1)=[O:5])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 57852687HCID 57852687, compound

Product 1

HCID 57852682HCID 57852682, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11-(2-Hydroxy-ethyl)-6,11-dihydro-5-thia-11-aza-benzo[α]fluorene-6-carboxylic acid diethylamide (iv) (100 mg, 0.26 mmol) in anhydrous dichloromethane 3 ml was added toluenesulfonyl chloride (100 mg, 0.52 mmol) and pyridine (0.2 ml, 2.6 mmol) at 0° C. under nitrogen. The reaction mixture was then stirred at room temperature for 48 hours. After quenched with 20 ml water, the mixture was extracted with dichloromethane 2×20 ml. The organic was dried (MgSO4) and removed in vacuo. The residue was purified by flash column chromatography over silica using a gradient 20% mixture of ethyl acetate and hexane to 40% ethyl acetate as eluant. Appropriate fractions were combined and the solvent was removed in vacuo to give the product 11-(2-Tosyloxy-ethyl)-6,11-dihydro-5-thia-11-aza-benzo[α]fluorene-6-carboxylic acid diethylamide (Compound 10P) as a white solid 98 mg. Yield 48%.

Workup

  1. customAfter quenched with 20 ml water
  2. extractionthe mixture was extracted with dichloromethane 2×20 ml
  3. dry with materialThe organic was dried (MgSO4)
  4. customremoved in vacuo
  5. customThe residue was purified by flash column chromatography over silica using a gradient 20% mixture of ethyl acetate and hexane to 40% ethyl acetate as eluant
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4e5137a527b34b08ac51ce59cbcae906
Source dataset
uspto-grants-2013_08
Patent number
US08506932B2

Reaction notes

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