Pivaloyl chloride → N-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-2-(3-fluorophenyl)pyrimidine-5-carboxamide

HRID 729638노트

반응식

HRID 729638 반응식
[NH:1]1[CH2:4][CH:3]([NH:5][C:6]([C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)=[N:12][CH:13]=2)=[O:7])[CH2:2]1.CCN(C(C)C)C(C)C.[C:30](Cl)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C>[CH3:32][C:31]([CH3:34])([CH3:33])[C:30]([N:1]1[CH2:4][CH:3]([NH:5][C:6]([C:8]2[CH:13]=[N:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)=[N:10][CH:9]=2)=[O:7])[CH2:2]1)=[O:35]

참가 물질

5

반응물 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 57832989N-azetidin-3-yl-2-(3-fluorophenyl)pyrimidine-5-carboxamide

생성물 1

HCID 57833074N-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-2-(3-fluorophenyl)pyrimidine-5-carboxamide수율 87.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-azetidin-3-yl-2-(3-fluorophenyl)pyrimidine-5-carboxamide (50 mg, 0.16 mmol) in DMF (1.0 mL) was added DIPEA (0.06 mL, 0.32 mmol) and pivaloyl chloride (30 mg, 0.24 mmol). The mixtures were stirred at room temperature overnight. The mixture was partitioned between ethyl acetate and brine. The organic layer was dried (MgSO4), filtered and concentrated to give a solid, which was purified by chromatography (silica, 80% EtOAc/Hex) to give the product, N-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-2-(3-fluorophenyl)pyrimidine-5-carboxamide (50 mg, 86%). HRMS (M+H)=357.1727 expected, observed=357.1799.

후처리

  1. customThe mixture was partitioned between ethyl acetate and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a solid, which
  6. customwas purified by chromatography (silica, 80% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-13325d92b4e44985bb0e712cf0190601
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582643B2

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