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Triethylamine → 3,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

HRID 2234041
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HRID 2234041 반응식
Cl.[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11].[Cl:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[CH:22][N:21]=1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.O>[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:22]2[CH:23]=[CH:24][N:25]=[C:20]([Cl:19])[N:21]=2)[CH2:15][CH2:14]1)=[O:11]
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 68579996HCID 68579996, 화합물2회

생성물 1

HCID 866083433,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide수율 57%

시약·촉매·용매 3

HCID 962Water용매
HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

3,4-Dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1, 650 mg, 2.08 mmol), 2,4-dichloropyrimidine (309.7 mg, 2.08 mmol), and Et3N (0.6 ml, 4.16 mmol) were combined in DMF (12 ml) and heated at 90° C. under nitrogen for 1.5 h. Upon cooling to room temperature, the reaction was diluted with EtOAc and water. The phases were separated, and the aqueous portion was extracted twice with EtOAc. The combined organic portions were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a light brown solid. The crude material was triturated with cold MeOH and filtered to give 458 mg (1.18 mmol, 57%) of the title product.

후처리

  1. temperatureUpon cooling to room temperature
  2. customThe phases were separated
  3. extractionthe aqueous portion was extracted twice with EtOAc
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a light brown solid
  9. customThe crude material was triturated with cold MeOH
  10. filtrationfiltered

출처 및 근거

ORD 기록
ord-4efd95c46d8143f1b7a1a4958292d895
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709503B2

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