Pyridine → HCID 68431394, compound

HRID 2244039Notes

Reaction equation

HRID 2244039 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:13][C:14]1[CH:15]=[C:16]([CH:32]=[CH:33][CH:34]=1)[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=1[CH2:29][CH2:30][CH3:31].N1C=CC=CC=1>ClCCl>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][C:16]2[CH:15]=[C:14]([NH:13][S:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=3)(=[O:11])=[O:10])[CH:34]=[CH:33][CH:32]=2)=[C:20]([CH2:29][CH2:30][CH3:31])[C:21]=1[OH:28])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 145235601-{4-[(3-Aminophenyl)methoxy]-2-hydroxy-3-propylphenyl}ethan-1-one

Product 1

HCID 68431394HCID 68431394, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 3-cyano-benzenesulfonyl chloride (673 mg, 3.34 mmol) to a solution of 1-[4-(3-amino-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone (1.00 g, 3.34 mmol) and pyridine (0.98 mL) in dichloromethane (20 mL) at 0° C. Warm to room temperature. Partition the mixture between dichloromethane and 2N hydrochloric acid (60 mL). Wash the organic layer with saturated sodium bicarbonate and brine. Dry and concentrate to afford the title compound as an orange solid (1.65 g): 1H NMR (DMSO-d6) δ 0.85 (t, 3H), 1.47 (sextet, 2H), 2.55 (t, 2H), 2.57 (s, 3H), 5.19 (s, 2H), 6.62 (d, 1H), 7.05 (d, 1H), 7.14 (d, 1H), 7.23 (s, 1H), 7.29 (t, 1H), 7.73 (t, 1H), 7.77 (d, 1H), 7.98 (d, 1H), 8.07 (d, 1H) 8.12 (s, 1H), 10.55 (s, 1H), 12.86 (s, 1H).

Workup

  1. customPartition the mixture between dichloromethane and 2N hydrochloric acid (60 mL)
  2. washWash the organic layer with saturated sodium bicarbonate and brine
  3. customDry
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-e6c0de99d924462b820256818132b3ce
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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