Acetyl chloride → HCID 86761254, compound

HRID 252706Notes

Reaction equation

HRID 252706 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[N:10][C:9]=2[CH3:17])=[CH:4][C:3]=1[NH:18][S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20].C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>C1COCC1>[C:14]([NH:13][C:11]1[S:12][C:8]([C:5]2[CH:4]=[C:3]([N:18]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:20])=[O:21])[C:35](=[O:37])[CH3:36])[C:2]([Cl:1])=[N:7][CH:6]=2)=[C:9]([CH3:17])[N:10]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11541283HCID 11541283, compound

Product 1

HCID 86761254HCID 86761254, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-{5-[6-Chloro-5-(phenylsulfonylamino)pyridin-3-yl]-4-methyl-1,3-thiazol-2-yl)acetamide was dissolved in THF. Triethylamine (0.113 mL, 0.811 mmol) was added. The solution was placed in an ice-bath and acetyl chloride (0.058 mL, 0.81 mmol) was added dropwise. The mixture was stirred at room temperature for 2 hours and then evaporated. Water and ethyl acetate were added. The organic phase was dried with magnesium sulfate, filtered and evaporated. The reaction product was purified by preparative HPLC (Method A) to give the title product (retention time 9.2 minutes) in 91% yield; 1H NMR Spectrum: (DMSOd6) 12.33 (1H, s); 8.69 (1H, d); 8.24 (1H, d); 8.06-8.00 (2H, m); 7.82 (1H, t); 7.72-7.67 (2H); 2.42 (3H, s); 2.17 (3H, s); 1.96 (3H, s); Mass Spectrum: M+H+ 465 and 467.

Workup

  1. customThe solution was placed in an ice-bath
  2. customevaporated
  3. additionWater and ethyl acetate were added
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe reaction product was purified by preparative HPLC (Method A)

Sources & evidence

ORD record
ord-70d51c22253d40d1b6878708c8c6718a
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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