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Water → 3-chloromethyl-N-[5-(3,5-difluoro-benzyloxy)-1H-indazol-3-yl]-benzamide

HRID 1803853
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인쇄 미리보기

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HRID 1803853 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([F:20])[CH:19]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[NH2:16].[Cl:21][CH2:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27].O>CC1C=C(C)N=C(C)C=1>[Cl:21][CH2:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([NH:16][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([O:6][CH2:5][C:4]3[CH:17]=[C:18]([F:20])[CH:19]=[C:2]([F:1])[CH:3]=3)[CH:8]=2)[NH:12][N:11]=1)=[O:27]
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참가 물질

5

반응물 3

HCID 962WaterHCID 27333243-(Chloromethyl)benzoyl chlorideHCID 669970485-[(3,5-difluorobenzyl)oxy]-1H-indazol-3-amine

생성물 1

HCID 462448313-chloromethyl-N-[5-(3,5-difluoro-benzyloxy)-1H-indazol-3-yl]-benzamide수율 56%

시약·촉매·용매 1

HCID 79532,4,6-Trimethylpyridine용매

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온도
4 °C

실험 절차

5-(3,5-Difluoro-benzyloxy)-1H-indazol-3-ylamine (550 mg, 2 mmol) was dissolved in sym-collidine, cooled to 4° C. and treated with neat 3-chloromethyl-benzoyl chloride (0.34 mL, 2.4 mmol). After 1 hour the reaction mixture was added drop wise into iced water, with stirring and separation of a yellow oil occurred. Then, EtOAc (50 mL) and 2N HCl (25 mL) were added. The organic phase was separated, washed with aqueous NaHCO3 (50 mL), brine, dried over sodium sulfate and evaporated to dryness. After purification over silica gel (eluent: DCM:MeOH 95:5) 378 mg of title compound were obtained as a whitish solid in 56% yield.

후처리

  1. customseparation of a yellow oil
  2. additionThen, EtOAc (50 mL) and 2N HCl (25 mL) were added
  3. customThe organic phase was separated
  4. washwashed with aqueous NaHCO3 (50 mL), brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customAfter purification over silica gel (eluent: DCM:MeOH 95:5) 378 mg of title compound
  8. customwere obtained as a whitish solid in 56% yield

출처 및 근거

ORD 기록
ord-f75a9373fc1446e1beb6364fdd07b40d
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08354399B2

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