Hydrochloric Acid → HCID 59321498, 화합물

HRID 2423465노트

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HRID 2423465 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]([CH2:16][C:17]1[C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[C:32]4[C:37](=[CH:38][CH:39]=3)[N:36]=[C:35]([C:40]([O:42]C)=[O:41])[CH:34]=[CH:33]4)=[CH:26][CH:25]=2)=[C:20]([CH:44]([CH3:46])[CH3:45])[O:19][N:18]=1)C(=O)C(F)(F)F.O1CCCC1.[OH-].[Na+].Cl>O.CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][CH2:16][C:17]1[C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[C:32]4[C:37](=[CH:38][CH:39]=3)[N:36]=[C:35]([C:40]([OH:42])=[O:41])[CH:34]=[CH:33]4)=[CH:26][CH:25]=2)=[C:20]([CH:44]([CH3:46])[CH3:45])[O:19][N:18]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321544Methyl 6-[4-({[3-{[(2,6-dichlorophenyl)(trifluoroacetyl)amino]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

생성물 1

HCID 59321498HCID 59321498, 화합물수율 100%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
90 °C

실험 절차

To a solution of methyl 6-[4-({[3-{[(2,6-dichlorophenyl)(trifluoroacetyl)amino]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (10 mg, 0.015 mmol) in 1:1 tetrahydrofuran:methanol (0.75 mL) was added 1 N sodium hydroxide (0.37 mL, 0.37 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes. The solution was concentrated and the residue was taken up with ethyl acetate. Then 1 N hydrochloric acid (0.37 mL, 0.37 mmol) was added followed by water. The layers were separated and the aqueous layer was extracted one more time with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated to afford 6-[4-({[3-{[(2,6-dichlorophenyl)amino]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (8 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ 8.46 (d, J=9 Hz, 1H), 8.31-8.24 (m, 2H), 8.11-8.07 (m, 2H), 7.69 (d, J=9 Hz, 2H), 7.25-7.20 (m, 2H), 7.07 (d, J=9 Hz, 2H), 6.84-6.80 (m, 1H), 4.96 (s, 2H), 4.60 (s, 2H), 3.24 (septet, J=7 Hz, 1H), 1.36 (d, J=7 Hz, 6H). HRMS (ESI) C30H25Cl2N3O4 calculated: 562.1300 (M+H)+, found: 562.1292 (M+H)+.

후처리

  1. concentrationThe solution was concentrated
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted one more time with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-422f5dfe447949ce8b7348c7b1e1e8bc
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

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