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Lithium Hydroxide → 6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-(tetrahydro-pyran-2-ylmethyl)-3H-benzoimidazole-5-carboxylic acid

HRID 217037
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HRID 217037 반응식
C[O:2][C:3]([C:5]1[C:20]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=2[Cl:29])=[C:19]([F:30])[C:8]2[N:9]=[CH:10][N:11]([CH2:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[C:7]=2[CH:6]=1)=[O:4].O1CCCC1.O.[Li+].[OH-]>O.Cl.C(OCC)(=O)C.O1CCCC1>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:20]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]3[N:11]([CH2:12][CH:13]4[CH2:18][CH2:17][CH2:16][CH2:15][O:14]4)[CH:10]=[N:9][C:8]=3[C:19]=2[F:30])=[C:23]([Cl:29])[CH:24]=1
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참가 물질

7

반응물 3

HCID 3939Lithium HydroxideHCID 21881883Oxolane--water (1/1)HCID 688190776-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-(tetrahydro-pyran-2-ylmethyl)-3H-benzoimidazole-5-carboxylic acid methyl ester

생성물 1

HCID 211141606-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-(tetrahydro-pyran-2-ylmethyl)-3H-benzoimidazole-5-carboxylic acid수율 100%

시약·촉매·용매 3

HCID 313
Hydrochloric Acid
용매
HCID 962Water용매2회
HCID 21939870Tetrahydrofuran ethyl acetate용매

실험 절차

6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-(tetrahydro-pyran-2-ylmethyl)-3H-benzoimidazole-5-carboxylic acid methyl ester 11q is suspended in 4:1 tetrahydrofuran/water (2.5 mL) and aqueous 1 M LiOH is added (2.5 mL). After stirring at room temperature for 16 hours, the reaction mixture is homogeneous and the reaction is complete. The reaction mixture is cooled to 0° C., diluted with water and aqueous 2 M HCl is added dropwise until the pH of the solution is 1-2, at which time it turns to a suspension. The reaction mixture is poured into a separatory funnel and diluted with ethyl acetate/tetrahydrofuran and water and the layers separated. The aqueous layer is extracted with ethyl acetate. The combined organic layers are washed with brine, dried (Na2SO4) and concentrated under reduced pressure to yield 0.11 g (100%) of the pure desired product as a white solid. MS ESI (+) m/z 482, 484 (M+, Br pattern) detected.

후처리

  1. additionis added (2.5 mL)
  2. temperatureThe reaction mixture is cooled to 0° C.
  3. additionis added dropwise until the pH of the solution
  4. additionThe reaction mixture is poured into a separatory funnel
  5. customthe layers separated
  6. extractionThe aqueous layer is extracted with ethyl acetate
  7. washThe combined organic layers are washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9975ac23dd1545d08eef92b5eb6f4973
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193231B2

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