Diisopropylethylamine → (R)-3-(5-bromo-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1094255노트

반응식

HRID 1094255 반응식
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[Br:15][C:16]1[CH:17]=[N:18][C:19](Cl)=[N:20][CH:21]=1.CCN(C(C)C)C(C)C.CC(=O)OCC.CCCCCCC>CCO.CC(=O)OCC>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([NH:1][C:19]2[N:20]=[CH:21][C:16]([Br:15])=[CH:17][N:18]=2)[CH2:3]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 21899848Ethylacetate heptane

생성물 1

HCID 66639558(R)-3-(5-bromo-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester수율 48%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (R)-3-amino-1-N-Boc-piperidine (920 mg) in dry EtOH (20 mL) were added successively 5-bromo-2-chloropyrimidine (957 mg), DIEA (0.86 mL). The reaction mixture was stirred at reflux for 16 hours under nitrogen. After cooling to RT, the reaction mixture was diluted with EA, washed with sat. NaHCO3, 1N NaOH. The organic extract was dried (MgSO4), filtered and concentrated to yield a crude brown-orange oil. FC (EA/n-heptane: 2/8) gave 787 mg (48%) of the title compound as a light brown solid.

후처리

  1. temperatureat reflux for 16 hours under nitrogen
  2. washwashed with sat. NaHCO3, 1N NaOH
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude brown-orange oil

출처 및 근거

ORD 기록
ord-bc11a06f67ad407e8f83f67990e20913
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133901B2

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