4-Chlorobenzenesulfonyl chloride → HCID 51354883, compound

HRID 2077551Notes

Reaction equation

HRID 2077551 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:21]=[CH:20][C:12]3[N:13]=[C:14]([NH:16][C:17](=[O:19])[CH3:18])[S:15][C:11]=3[CH:10]=2)[CH:5]=[N:6][C:7]=1[Cl:8].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>N1C=CC=CC=1.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:8][C:7]1[N:6]=[CH:5][C:4]([C:9]2[CH:21]=[CH:20][C:12]3[N:13]=[C:14]([NH:16][C:17](=[O:19])[CH3:18])[S:15][C:11]=3[CH:10]=2)=[CH:3][C:2]=1[NH:1][S:29]([C:26]1[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=1)(=[O:31])=[O:30]

Participants

6

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 51355176HCID 51355176, compound

Product 1

HCID 51354883HCID 51354883, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

N-(6-(5-amino-6-chloropyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.040 g, 0.13 mmol) was dissolved in pyridine (1 ml), then 4-chlorobenzene-1-sulfonyl chloride (0.026 g, 0.13 mmol) was added to the mixture while stirring. The mixture was allowed to stir under inert atmosphere for 3 days. The progress of the reaction was monitored by LC/MS, which showed product. The mixture was diluted with DCM and saturated sodium bicarbonate solution. The organic layer was extracted with DCM (3×20 ml). Combined organics, dried over sodium sulfate, filtered and concentrated in vacuo. The crude was purified by ISCO silica-gel chromatography in a gradient of 0-10% Methanol/DCM. The fractions with desired material were combined and concentrated in vacuo. The residue was diluted with ethyl acetate and allowed to stir 10 minutes. The precipitate was collected by filtration and washed with 1:1 ethyl acetate/hexanes to give N-(6-(6-chloro-5-(4-chlorophenylsulfonamido)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.015 g, 24% yield) as a white crystalline solid. MS (ESI pos. ion) m/z: 494 (MH+). Calc'd exact mass for C20H14Cl2N4O3S2: 493. 1H NMR (400 MHz, DMSO-d6): 2.23 (s, 3H), 5.73 (s, 1H), 7.48-8.17 (m, 7H), 8.84 (s, 1H), 8.62 (s, 1H), 12.45 (s, 1H).

Workup

  1. stirringto stir under inert atmosphere for 3 days
  2. extractionThe organic layer was extracted with DCM (3×20 ml)
  3. dry with materialCombined organics, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by ISCO silica-gel chromatography in a gradient of 0-10% Methanol/DCM
  7. concentrationconcentrated in vacuo
  8. additionThe residue was diluted with ethyl acetate
  9. stirringto stir 10 minutes
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d61134db306645db89c942b00409b510
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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