Hydrochloric Acid → 6-[4-({[3-{[(2,6-Dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid

HRID 2423470노트

반응식

HRID 2423470 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9][CH2:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([C:34]([O:36]CC)=[O:35])[CH:28]=[CH:27]4)=[CH:20][CH:19]=2)=[C:14]([CH:39]([CH3:41])[CH3:40])[O:13][N:12]=1.O1CCCC1.[OH-].[Na+].Cl>CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9][CH2:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([C:34]([OH:36])=[O:35])[CH:28]=[CH:27]4)=[CH:22][CH:23]=2)=[C:14]([CH:39]([CH3:41])[CH3:40])[O:13][N:12]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321572Ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

생성물 1

HCID 593215486-[4-({[3-{[(2,6-Dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid수율 107.9%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
90 °C

실험 절차

To a solution of ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (5 mg, 0.008 mmol) in 1:1 tetrahydrofuran:methanol (0.5 mL) was added 1 N sodium hydroxide (0.04 mL, 0.04 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes and 1 N hydrochloric acid (0.04 mL, 0.04 mmol) was added. The mixture was concentrated and the residue was taken up with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated to afford 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (5 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ 8.44 (d, J=9 Hz, 1H), 8.29 (d, J=9 Hz, 1H), 8.21 (d, J=9 Hz, 1H), 8.10-8.07 (m, 2H), 7.70 (d, J=9 Hz, 2H), 7.34-7.14 (m, 3H), 7.10 (d, J=9 Hz, 2H), 5.08 (s, 2H), 4.16 (s, 2H), 3.20 (septet, J=7 Hz, 1H), 1.32 (d, J=7 Hz, 6H). HRMS (ESI) C30H24Cl2N2O4S calculated: 579.0912 (M+H)+, found: 579.0925 (M+H)+.

후처리

  1. concentrationThe mixture was concentrated
  2. washwashed with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ebd493b7d90144d9bd4309c2c522f1d7
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

반응 노트

불러오는 중…