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

HRID 1803853
ノート
印刷プレビュー

反応式

HRID 1803853 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 79532,4,6-Trimethylpyridine溶媒

反応条件

温度
4 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f75a9373fc1446e1beb6364fdd07b40d
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08354399B2

反応ノート

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