Pyridine → HCID 21930318, compound

HRID 1243662

Reaction equation

HRID 1243662 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])=[O:5].N1C=CC=CC=1.[N+:27]([C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:31]=1[S:40](Cl)(=[O:42])=[O:41])([O-:29])=[O:28]>ClCCl.C(OCC)(=O)C>[Br:20][C:17]1[CH:18]=[CH:19][C:2]([NH:1][S:40]([C:31]2[CH:32]=[CH:33][C:34]([C:36]([F:38])([F:39])[F:37])=[CH:35][C:30]=2[N+:27]([O-:29])=[O:28])(=[O:41])=[O:42])=[C:3]([CH:16]=1)[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])=[O:5]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27757802-Nitro-4-(trifluoromethyl)benzene-1-sulfonyl chlorideHCID 219302782-Amino-5-bromo-N-(2-methoxy-benzyl)-benzamide

Product 1

HCID 21930318HCID 21930318, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

2-Amino-5-bromo-N-(2-methoxy-benzyl)-benzamide (9 g, 28 mmol) was suspended in anhydrous dichloromethane (300 ml) and cooled in ice bath. Pyridine (20 ml) was added with stirring, followed by addition of 2-nitro-4-trifluoromethyl-benzene sulfonyl chloride (15 g, 52 mmol). The reaction mixture was allowed to stir at room temperature for 2 days. The mixture was filtered to remove a solid precipitate and the filtrate was evaporated to dryness. Aqueous HCl (2N, 300 ml) was added, and the resulting solution was extracted with dichloromethane (500 ml). The organic layer was concentrated and the resulting residue was dissolved in ethyl acetate. Addition of hexanes to this solution produced a solid precipitate. This solid was dissolved in ethyl acetate and passed through a short column of silica using an eluent of dichloromethane and ethyl acetate to provide the desired product (7.5 g, 46% yield). M/Z of [M−H]−=587.1 1H NMR (DMSO) δ=3.8 (s, 3H), 4.35 (sd, 2H), 6.85 (1H), 6.95 (1H), 7.1 (1H), 7.2 (1H), 7.4 (1H), 7.65 (1H), 8 (1H), 8.15 (1H), 8.25 (1H), 8.55 (1H).

Workup

  1. temperaturecooled in ice bath
  2. stirringto stir at room temperature for 2 days
  3. filtrationThe mixture was filtered
  4. customto remove a solid precipitate
  5. customthe filtrate was evaporated to dryness
  6. additionAqueous HCl (2N, 300 ml) was added
  7. extractionthe resulting solution was extracted with dichloromethane (500 ml)
  8. concentrationThe organic layer was concentrated
  9. dissolutionthe resulting residue was dissolved in ethyl acetate
  10. additionAddition of hexanes to this solution
  11. customproduced a solid precipitate

Sources & evidence

ORD record
ord-34bd1e26085d4ed7a58ca0c6416504e8
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Linked notes

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