2-[(4-Methylphenyl)sulfonyl]-3-pyridinamine → HCID 57856155, compound

HRID 2401951Notes

Reaction equation

HRID 2401951 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13](Cl)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[S:16]([C:26]1[C:31]([NH2:32])=[CH:30][CH:29]=[CH:28][N:27]=1)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>N1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:32][C:31]4[C:26]([S:16]([C:19]5[CH:20]=[CH:21][C:22]([CH3:23])=[CH:24][CH:25]=5)(=[O:18])=[O:17])=[N:27][CH:28]=[CH:29][CH:30]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 14723442-[(4-Methylphenyl)sulfonyl]-3-pyridinamineHCID 591291541-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

Product 1

HCID 57856155HCID 57856155, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

To 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (45 mg, 0.2 mmol) in pyridine (2 mL) was added 2-tosylpyridin-3-amine (50 mg, 0.2 mmol) and the reaction mixture was stirred at 115° C. for 15 hours. The solvent was evaporated to dryness and the residue redissolved in DMF, filtered and purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoracetic acid to yield the pure product. ESI-MS m/z calc. 436.5, found 437.1 (M+1)+. Retention time 3.16 minutes.

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionthe residue redissolved in DMF
  3. filtrationfiltered
  4. custompurified by reverse-phase preparative liquid chromatography
  5. customto yield the pure product

Sources & evidence

ORD record
ord-63cf5fbbfeaf435eb05d5150b59c416a
Source dataset
uspto-grants-2014_08
Patent number
US08796312B2

Reaction notes

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