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1-Bromo-2-methylpropane → N-(6-(1-benzylpyrrolidin-3-yl)-2-methylpyridin-3-yl)-4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutylbenzenesulfonamide

HRID 594136
ノート
印刷プレビュー

反応式

HRID 594136 の反応式
[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[C:20]([CH3:37])=[N:21][C:22]([CH:25]4[CH2:29][CH2:28][N:27]([CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:26]4)=[CH:23][CH:24]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:38])[O:4][N:3]=1.[CH3:39][C:40](N=C(N(C)C)N(C)C)([CH3:42])[CH3:41].BrCC(C)C>C(#N)C>[CH2:30]([N:27]1[CH2:28][CH2:29][CH:25]([C:22]2[N:21]=[C:20]([CH3:37])[C:19]([N:18]([CH2:39][CH:40]([CH3:42])[CH3:41])[S:15]([C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[CH3:38])=[CH:14][CH:13]=3)(=[O:16])=[O:17])=[CH:24][CH:23]=2)[CH2:26]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1
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 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898763124-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-{2-methyl-6-[1-(phenylmethyl)-3-pyrrolidinyl]-3-pyridinyl}benzenesulfonamide

生成物 1

HCID 117925766N-(6-(1-benzylpyrrolidin-3-yl)-2-methylpyridin-3-yl)-4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutylbenzenesulfonamide収率 48.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-{2-methyl-6-[1-(phenylmethyl)-3-pyrrolidinyl]-3-pyridinyl}benzenesulfonamide (211 mg, 0.396 mmol) and N″-(1,1-dimethylethyl)-N,N,N′,N′-tetramethylguanidine (67.9 mg, 0.396 mmol) in acetonitrile (3 mL) was added 1-bromo-2-methylpropane (0.086 mL, 0.792 mmol). The reaction vessel was sealed and heated at 80° C. for 8 hours. The reaction mixture was separated between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was washed with brine and dried over magnesium sulphate. The solvent was removed in vacuo. The sample was purified by flash silica (Si) chromatography (0-25% methanol-dichloromethane gradient). The appropriate fractions were combined and evaporated in vacuo to give the required product (114 mg) as a brown gum. LCMS (2 min, formic) Rt 1.01 min, m/z (ES+) 589 (M+H)

後処理

  1. customThe reaction vessel was sealed
  2. customThe reaction mixture was separated between ethyl acetate and saturated sodium bicarbonate solution
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was removed in vacuo
  6. customThe sample was purified by flash silica (Si) chromatography (0-25% methanol-dichloromethane gradient)
  7. customevaporated in vacuo

出典と根拠

ORDレコード
ord-2eeafdb7b16949bda4cf8ee3cb6aa7f5
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242972B2

反応ノート

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