Sodium Hydroxide → 4-[({[5-Fluoro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)methyl]benzoic acid

HRID 1293162노트

반응식

HRID 1293162 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=2)=[O:17])[C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:28][CH:29]=2)=[O:17])[C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 57572271HCID 57572271, 화합물

생성물 1

HCID 589053584-[({[5-Fluoro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)methyl]benzoic acid수율 64%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of methyl 4-[({[5-fluoro-2-(4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)methyl]benzoate (step 3, 407 mg, 1.02 mmol) in methanol (10 ml)_was added 2 N sodium hydroxide aqueous solution (2 mL). The reaction mixture was stirred at room temperature for 3 h and then evaporated. The residue was partitioned between ethyl acetate (100 mL) and 2 N hydrochloric acid (100 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic extracts were washed with brine (50 mL), dried (sodium_sulfate), and concentrated. The residual solids were recrystallized from ethyl acetate to afford 248 mg (64%) of the title compound as white solids: 1H-NMR (CDCl3) δ 8.40 (1H, dd, J=8.3, 3.1 Hz), 8.30 (1H, br.s), 8.09–8.04 (3H, m), 7.45 (2H, d, J=8.1 Hz), 7.17–7.06 (4H, m), 4.79 (2H, d, J=5.9 Hz); MS (EI) m/z 384 (M+), (ESI) m/z 385 (M+H)+, 383 (M−H)−.

후처리

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate (100 mL) and 2 N hydrochloric acid (100 mL)
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (100 mL)
  5. washThe combined organic extracts were washed with brine (50 mL)
  6. dry with materialdried (sodium_sulfate)
  7. concentrationconcentrated
  8. customThe residual solids were recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-eeec290c7ae448adbf2d6c96ee46b701
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238714B2

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