Triethylamine → 5-Bromo-3-(2-chloro-ethyl)-thiophene-2-carboxylic acid [4-((R)-3-dimethylamino-pyrrolidin-1-yl)-phenyl]-amide

HRID 69504ノート

反応式

HRID 69504 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([N:13]([CH3:15])[CH3:14])[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:23][C:24]1[S:28][C:27]([C:29](Cl)=[O:30])=[C:26]([CH2:32][CH2:33][Cl:34])[CH:25]=1>C1COCC1>[CH3:14][N:13]([CH3:15])[C@@H:10]1[CH2:11][CH2:12][N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:29]([C:27]3[S:28][C:24]([Br:23])=[CH:25][C:26]=3[CH2:32][CH2:33][Cl:34])=[O:30])=[CH:3][CH:4]=2)[CH2:9]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 59815627[(R)-1-(4-aminophenyl)pyrrolidin-3-yl]dimethylamineHCID 866351075-Bromo-3-(2-chloro-ethyl)-thiophene-2-carbonyl chloride

生成物 1

HCID 866351065-Bromo-3-(2-chloro-ethyl)-thiophene-2-carboxylic acid [4-((R)-3-dimethylamino-pyrrolidin-1-yl)-phenyl]-amide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of [(R)-1-(4-Amino-phenyl)-pyrrolidin-3-yl]-dimethyl-amine (349 mg) and triethylamine (0.25 mL) in THF (4 mL) a solution of 5-Bromo-3-(2-chloro-ethyl)-thiophene-2-carbonyl chloride (489.6 mg) in THF (3 mL) added dropwise. The mixture was stirred for 2 h at room temperature. Then the solvent was removed in vacuum and then water and ethyl acetate were added to the residue. The aqueous phase was extracted with ethyl acetate three times. The combined organic phases were dried over sodium sulfate and the solvent was removed in vacuum. In this way the product was obtained with molecular weight 456.84 (C19H23BrClN3OS); MS (ESI): 456, 458 (M+H+).

後処理

  1. additionadded dropwise
  2. customThen the solvent was removed in vacuum
  3. additionwater and ethyl acetate were added to the residue
  4. extractionThe aqueous phase was extracted with ethyl acetate three times
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customthe solvent was removed in vacuum
  7. customIn this way the product was obtained with molecular weight 456.84 (C19H23BrClN3OS)

出典と根拠

ORDレコード
ord-fd047b3982ac48afb0bff700461f8660
出典データセット
uspto-grants-2014_09
特許番号
US08822495B2

反応ノート

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