Boron tribromide → HCID 58777582, 화합물

HRID 1371727노트

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HRID 1371727 반응식
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16]C)=[C:14]([O:18]C)[CH:13]=[C:12]([F:20])[C:11]=2[F:21])=[O:9])=[CH:6][N:5]=[C:4]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25][CH2:24]2)[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([OH:16])=[C:14]([OH:18])[CH:13]=[C:12]([F:20])[C:11]=2[F:21])=[O:9])=[CH:6][N:5]=[C:4]([NH:22][CH:23]2[CH2:24][CH2:25][N:26]([S:29]([CH3:32])(=[O:30])=[O:31])[CH2:27][CH2:28]2)[N:3]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 58777551HCID 58777551, 화합물

생성물 1

HCID 58777582HCID 58777582, 화합물수율 53.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-5,6-dimethoxy-phenyl)-methanone (100 mg, 0.212 mmol, Example 261) in methylene chloride (50 mL) cooled to −78° C. was added boron tribromide (2.19 mL, 2.190 mmol, 1 M solution in methylene chloride, Aldrich). The reaction mixture was warmed slowly to 0° C. over a period of 1 hour. After being stirred at 0° C. for 1 hour, the reaction was quenched with a solution of aqueous sodium bicarbonate. The aqueous layer was extracted with methylene chloride. The combined layers were washed with water and dried over anhydrous sodium sulfate. The solids were filtered off and the filtrate was concentrated in vacuo. Purification of the crude residue by reversed phase HPLC (C18, eluting with water and acetonitrile) yielded [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-5,6-dihydroxy-phenyl)-methanone as yellow solids (50 mg, 52%). HR-MS (ES, m/z) calculated for C17H20N5O5SF2 [(M+H)+] 444.1151, observed 444.1148.

후처리

  1. customthe reaction was quenched with a solution of aqueous sodium bicarbonate
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. washThe combined layers were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customPurification of the crude residue
  8. washby reversed phase HPLC (C18, eluting with water and acetonitrile)

출처 및 근거

ORD 기록
ord-20fd62284a3d44c2a046f8c90853c1c9
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157455B2

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