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

HRID 69504노트

반응식

HRID 69504 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-fd047b3982ac48afb0bff700461f8660
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822495B2

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