Pyridine → HCID 58599184, compound

HRID 2378041Notes

Reaction equation

HRID 2378041 reaction equation
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)(=[O:21])[CH3:20]>C1COCC1>[C:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([NH:12][CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)(=[O:30])=[O:29])=[CH:26][CH:27]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 83551-NaphthalenemethanamineHCID 2664184-Acetylbenzenesulfonyl chloride

Product 1

HCID 58599184HCID 58599184, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Napthalene-methylamine (1.118 g, 7.11 mmol) was dissolved in THF before pyridine (1.725 ml, 21.3 mmol) was added. 4-Acetyl-benzenesulfonyl chloride (1.554 g, 7.11 mmol) was then added as a solid, and the resulting dark solution was stirred for 10 minutes. The volatiles were then removed, and the resulting residue was suspended in THF. Excess Et3N was then added, and the mixture was stirred for several minutes before the solids were filtered. The mother liquor was then evaporated to a solid which was recrystalized in ethylacetate and hexanes to yield 0.5697 g (0.00167 mol, 23%) of desired compound that was pure enough for the next step. LC-MS (ES+): 340 [MH]+ m/e.

Workup

  1. additionwas added
  2. customThe volatiles were then removed
  3. additionExcess Et3N was then added
  4. stirringthe mixture was stirred for several minutes before the solids
  5. filtrationwere filtered
  6. customThe mother liquor was then evaporated to a solid which
  7. customwas recrystalized in ethylacetate

Sources & evidence

ORD record
ord-33e581f216154c8ba2191c9b08f3552a
Source dataset
uspto-grants-2008_12
Patent number
US07470722B2

Reaction notes

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