Formic Acid → 2-Amino-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylic acid

HRID 573603ノート

反応式

HRID 573603 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[C:17]([C:18]([O:20]CC)=[O:19])=[C:16]([CH3:23])[N:15]=[C:14]3[S:24][C:25]([NH:35]C(OC(C)(C)C)=O)=[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=4)[C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].C(O)=O>CS(C)=O.O>[NH2:35][C:25]1[S:24][C:14]2=[N:15][C:16]([CH3:23])=[C:17]([C:18]([OH:20])=[O:19])[C:12]([NH:11][S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)(=[O:9])=[O:10])=[C:13]2[C:26]=1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=1

参加物

6

反応物 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 68380565Ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate

生成物 1

HCID 683238882-Amino-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylic acid収率 81.1%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

A mixture of ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate (Description 83) (600 mg, 0.949 mmol) and aqueous NaOH (2M) (2.373 mL, 4.75 mmol) in DMSO (10 mL) was heated at 150° C. for 40 min. After cooling to RT, the mixture was diluted with water (20 mL) and acidified with formic acid to pH 6. The mixture was then extracted with ethyl acetate (30 mL×5) and the combined organics concentrated. The residue was passed through a phase separator (C18 cartridge) eluting with water (20 mL×3) and MeOH (20 mL×5) and the combined methanolic fractions concentrated and dried, to give the title compound (388 mg). LCMS (A) m/z: 504 [M+1]+, Rt 1.17 min (acidic).

後処理

  1. temperatureAfter cooling to RT
  2. extractionThe mixture was then extracted with ethyl acetate (30 mL×5)
  3. washeluting with water (20 mL×3) and MeOH (20 mL×5)
  4. concentrationthe combined methanolic fractions concentrated
  5. customdried

出典と根拠

ORDレコード
ord-15d22a9e204946d890286a4015ba16a3
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

読み込み中…