Methanesulfonic Acid → 7-bromo-8-fluoro-3-(3-methoxy-3-methylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

HRID 335893노트

반응식

HRID 335893 반응식
[NH2:1][C:2]1[O:3][CH2:4][C:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]#[C:21][C:22]([CH3:25])([OH:24])[CH3:23])[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([Br:27])=[C:10]([F:26])[CH:11]=3)[N:6]=1.[CH3:28]S(O)(=O)=O.C([O-])(O)=O.[Na+]>CO>[Br:27][C:9]1[CH:8]=[C:7]2[C:5]3([CH2:4][O:3][C:2]([NH2:1])=[N:6]3)[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]#[C:21][C:22]([O:24][CH3:28])([CH3:23])[CH3:25])[CH:18]=3)[O:13][C:12]2=[CH:11][C:10]=1[F:26]

참가 물질

5

반응물 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 673829024-(2'-amino-7-bromo-8-fluoro-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-3-yl)-2-methylbut-3-yn-2-ol

생성물 1

HCID 673873667-bromo-8-fluoro-3-(3-methoxy-3-methylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 4-(2′-amino-7-bromo-8-fluoro-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-3-yl)-2-methylbut-3-yn-2-ol (0.580 g, 1.342 mmol) in 10 mL MeOH was treated with methanesulfonic acid (0.871 mL, 13.42 mmol). The resulting solution was allowed to stir at RT for 72 hours and was then heated at 85° C. for 3 hours. The reaction mixture was poured into saturated NaHCO3 (50 mL) and was extracted with EtOAc (3×25 mL). The organics were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the crude residue by column chromatgraphy [0-100% (95:5 EtOAc/MeOH)/CH2Cl2] afforded 7-bromo-8-fluoro-3-(3-methoxy-3-methylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine

후처리

  1. temperaturewas then heated at 85° C. for 3 hours
  2. extractionwas extracted with EtOAc (3×25 mL)
  3. washThe organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude residue by column chromatgraphy [0-100% (95:5 EtOAc/MeOH)/CH2Cl2]

출처 및 근거

ORD 기록
ord-1cf39d7711c4452eafa8b92bf93d7518
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883782B2

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