Sodium hydride → N-(3,4-Dimethyl-5-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-pyrimidinyl)[1,1-biphenyl]-2-sulfonamide

HRID 1956968ノート

反応式

HRID 1956968 の反応式
[CH3:1][C:2]1([CH3:8])[CH2:6][CH2:5][NH:4][C:3]1=[O:7].[H-].[Na+].Br[CH2:12][C:13]1[CH:18]=[C:17]([C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:16]=[CH:15][C:14]=1[C:25]1[C:26]([S:31]([N:34]([C:41]2[O:45][N:44]=[C:43]([CH3:46])[C:42]=2[CH3:47])COCCOC)(=[O:33])=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=1.CC1C(C)=C(NS(C2C(C3C=CC(C4N=CC=CN=4)=CC=3C=O)=CC=CC=2)(=O)=O)ON=1>CN(C)C=O.O>[CH3:46][C:43]1[C:42]([CH3:47])=[C:41]([NH:34][S:31]([C:26]2[C:25]([C:14]3[CH:15]=[CH:16][C:17]([C:19]4[N:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:18][C:13]=3[CH2:12][N:4]3[CH2:5][CH2:6][C:2]([CH3:8])([CH3:1])[C:3]3=[O:7])=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:33])=[O:32])[O:45][N:44]=1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 51149083,3-Dimethylpyrrolidin-2-oneHCID 18663185N-(3.4-Dimethyl-5-isoxazolyl)-2'-formyl-4'-(2-pyrimidinyl) [1,1-biphenyl]-2-sulfonamideHCID 186631932'-(Bromomethyl)-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-4'-(2-pyrimidinyl)[1,1'-biphenyl]-2-sulfonamide

生成物 1

HCID 18663183N-(3,4-Dimethyl-5-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-pyrimidinyl)[1,1-biphenyl]-2-sulfonamide収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the 3,3-dimethyl-2-pyrrolidinone so prepared (0.033 g, 0.29 mmol) in 1 mL of dimethylformamide ("DMF"), NaH (60% suspension in mineral oil, 0.015 g, 0.36 mmol) was added and the mixture was stirred at room temperature under argon for 10 minutes. 2'-(Bromomethyl)-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-4'-(2-pyrimidinyl)[1,1'-biphenyl]-2-sulfonamide (prepared as described in Step A of Example 14, except that the title compound of Step F of Example 11 was employed in place of N-(4,5-dimethyl-3-isoxazolyl)-2'-formyl-N-[(2-methoxyethoxy)methyl]-4'-(2-pyrimidinyl)[1,1'-biphenyl]-2-sulfonamide; 0.085 g, 0.145 mmol) was then added and the mixture was stirred for 3 hrs. The mixture was then added to 50 mL water and the solution was extracted with 3×25 mL EtOAc. The combined organic extracts were washed with water and dried and evaporated to afford 0.086 g (95%) of the title compound of this step as a colorless gum.

後処理

  1. addition0.085 g, 0.145 mmol) was then added
  2. stirringthe mixture was stirred for 3 hrs
  3. extractionthe solution was extracted with 3×25 mL EtOAc
  4. washThe combined organic extracts were washed with water
  5. customdried
  6. customevaporated

出典と根拠

ORDレコード
ord-f3201f663da842fc9fd8fdb14968add2
出典データセット
uspto-grants-1998_07
特許番号
US05780473

反応ノート

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