Acetyl chloride → N-{4-{[(3-Chlorophenyl)sulfonyl]amino}-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-2-yl}acetamide

HRID 573695Notes

Reaction equation

HRID 573695 reaction equation
[NH2:1][C:2]1[S:22][C:5]2=[N:6][C:7]([CH3:21])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[CH:8]=[C:7]([CH3:21])[N:6]=[C:5]3[S:22][C:2]([NH:1][C:38](=[O:40])[CH3:39])=[C:3]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)[C:4]=23)(=[O:12])=[O:13])[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 68324028N-{2-Amino-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide

Product 1

HCID 68323915N-{4-{[(3-Chlorophenyl)sulfonyl]amino}-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-2-yl}acetamideYield 13.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-{2-amino-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (Description 85) (40 mg, 0.087 mmol) in DCM (3 mL) was added triethylamine (0.036 mL, 0.261 mmol) and acetyl chloride (7.42 ul, 0.104 mmol) and the mixture stirred at RT for ca. 1 h. NaHCO3 solution (25 mL) was then added and the mixture extracted with DCM (20 mL×3) and the combined organics dried and concentrated. The residue was purified by normal phase chromatography, eluting with a gradient of 0-50% ethyl acetate in DCM and was then further purified by MDAP (acidic conditions), to give the title compound (5.8 mg). LCMS (A) m/z: 502 [M+1]+, Rt 1.05 min (acidic).

Workup

  1. extractionthe mixture extracted with DCM (20 mL×3)
  2. customthe combined organics dried
  3. concentrationconcentrated
  4. customThe residue was purified by normal phase chromatography
  5. washeluting with a gradient of 0-50% ethyl acetate in DCM
  6. customwas then further purified by MDAP (acidic conditions)

Sources & evidence

ORD record
ord-d70bfee0fe5c4b7f8beae37c49c3bbac
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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