Hydrochloric Acid → 2-(4-(5-(4-Chlorophenylsulfonamido)quinolin-6-yloxy)-3-methoxyphenyl)acetic acid

HRID 2423319노트

반응식

HRID 2423319 반응식
[NH2:1][C:2]1[C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][C:14]=2[O:25][CH3:26])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.N1C(C)=CC=CC=1C.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1.[OH-].[Na+].Cl>C1COCC1.CCOC(C)=O.O>[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([NH:1][C:2]2[C:11]([O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][C:14]=3[O:25][CH3:26])=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)(=[O:44])=[O:43])=[CH:38][CH:37]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 79372,6-LutidineHCID 14798Sodium HydroxideHCID 59864773Ethyl 2-(4-(5-aminoquinolin-6-yloxy)-3-methoxyphenyl)acetate

생성물 1

HCID 598648792-(4-(5-(4-Chlorophenylsulfonamido)quinolin-6-yloxy)-3-methoxyphenyl)acetic acid

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

To 24.4 (36 mg, 0.1 mmol) and 2,6-lutidine (0.024 mL, 0.2 mmol) in THF (0.5 mL) was added 4-chlorobenzenesulfonyl chloride (26 mg, 0.12 mmol). The mixture was stirred at 70° C. overnight. After cooling, water (1 mL) and 10N NaOH (0.5 mL) were added. The mixture was stirred at room temperature for 5 h. 3N HCl (1.7 mL) and EtOAc were added to the mixture, and the organic layer was separated, dried with MgSO4 and concentrated. Flash column chromatography of the residue afforded 24. MS ESI (pos.) m/z: 499.1 (M+H). 1H NMR (DMSO-d6) δ 10.2 (bs, 1H), 8.82 (d, 1H); 8.50 (d, 1H); 7.92 (d, 1H); 7.71 (d, 2H); 7.61 (dd, 1H); 7.55 (d, 2H); 7.03 (d, 1H); 6.95 (d, 1H); 6.79 (dd, 1H); 6.38 (d, 1H); 3.73 (s, 3H); 3.58 (s, 2H).

후처리

  1. temperatureAfter cooling
  2. stirringThe mixture was stirred at room temperature for 5 h
  3. customthe organic layer was separated
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c8f79682a8d845d8906e7780bca8aa60
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960567B2

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