Hydrochloric Acid → HCID 11583988, compound

HRID 1169836Notes

Reaction equation

HRID 1169836 reaction equation
[CH2:1]([NH:3][S:4](C1C=CC=CC=1O)(=[O:6])=[O:5])[CH3:2].[Cl:14][C:15]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:16]=1[C:17]([NH:19][CH2:20][C:21]1([C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:18].Cl>O1CCOCC1>[Cl:14][C:15]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:16]=1[C:17]([NH:19][CH2:20][C:21]1([C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:22][CH2:23][N:24]([S:4]([NH:3][CH2:1][CH3:2])(=[O:6])=[O:5])[CH2:25][CH2:26]1)=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 59003514HCID 59003514, compoundHCID 67172411HCID 67172411, compound

Product 1

HCID 11583988HCID 11583988, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-ethyl-2-hydroxyl-benzenesulfonamide (30 mg, 0.137 mmol) and 2,4-dichloro-N-{[4-(3-fluoropyridin-2-yl)piperidin-4-yl]methyl}benzamide (57.5 mg, 0.150 mmol) (prepared by the method in Example 1) in dioxane (2 ml) was refluxed under nitrogen for 4.5 hours. The mixture was allowed to cool then poured into 1 M HCl solution and extracted with diethyl ether (2×20 ml). The organic phase was washed with water (20 ml) and brine (20 ml), dried over MgSO4, filtered, and evaporated. The crude product was purified by preparatory TLC eluted with 50% ethyl acetate in isohexane to give the title product as a white foamy solid. 1H NMR δ (ppm)(CDCl3): 8.39-8.35 (1 H, m), 7.55 (1 H, d, J=8.4 Hz), 7.43-7.35 (2 H, m), 7.30-7.01 (2 H, m), 6.76-6.69 (1 H, m), 4.00-3.94 (3 H, m), 3.54-3.45 (2 H, m), 3.26-3.20 (2 H, m), 3.17-3.09 (2 H, m), 2.74-2.63 (2 H, m), 1.88-1.80 (2 H, m), 1.19 (3 H, t, J=7.2 Hz). m/e=489/491 (3:2).

Workup

  1. temperaturewas refluxed under nitrogen for 4.5 hours
  2. temperatureto cool
  3. extractionextracted with diethyl ether (2×20 ml)
  4. washThe organic phase was washed with water (20 ml) and brine (20 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by preparatory TLC
  9. washeluted with 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-12602d92294841ac80d9bb1369184249
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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