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

HRID 573695ノート

反応式

HRID 573695 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d70bfee0fe5c4b7f8beae37c49c3bbac
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

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