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

HRID 573603노트

반응식

HRID 573603 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
150 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-15d22a9e204946d890286a4015ba16a3
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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