Hydrochloric Acid → 5-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-hydroxy-ethoxy)-amide

HRID 2076217노트

반응식

HRID 2076217 반응식
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:27]=[N:28][CH:29]=2)[C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:25][CH2:24]2)=[CH:19][C:18]=1[F:26])=[O:9])=C.Cl>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[N:14]([CH:27]=[N:28][CH:29]=2)[C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:24][CH2:25]2)=[CH:19][C:18]=1[F:26])=[O:9]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 591401465-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-vinyloxy-ethoxy)-amide

생성물 1

HCID 441359805-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-hydroxy-ethoxy)-amide수율 41%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 5-(4-cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-vinyloxy-ethoxy)-amide (270 mg, 0.681 mmol) in methanol (10 mL) was added 1M hydrochloric acid (2 mL, 2 mmol.) and the mixture stirred at room temperature for 2 hours. Solvent was removed in vacuo, and then saturated aqueous NaHCO3 added and the mixture extracted with ethyl acetate. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was triturated with TBME and the solid collected by filtration to give the title compound as an off-white solid (103 mg, 41%). LCMS (Method A): RT5.68 [M+H] 371. 1HNMR (DMSO-d6, 400 MHz) 7.81 (1H, s), 7.37-7.34 (1H, m), 7.27 (1H, d, J=9.37 Hz), 6.95 (1H, d, J=9.34 Hz), 6.91 (1H, dd, J=12.49, 1.92 Hz), 6.75 (1H, dd, J=8.27, 1.96 Hz), 6.56-6.46 (1H, m), 3.71-3.65 (2H, m), 3.48-3.43 (2H, m), 1.89-1.80 (1H, m), 0.91-0.85 (2H, m), 0.65-0.57 (2H, m).

후처리

  1. customSolvent was removed in vacuo
  2. additionsaturated aqueous NaHCO3 added
  3. extractionthe mixture extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was triturated with TBME
  9. filtrationthe solid collected by filtration

출처 및 근거

ORD 기록
ord-09af48555294473b89ed2821032645fd
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923456B2

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