Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate → Methyl 2-(4-{[(4-bromo-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-chloroisonicotinate

HRID 2233938노트

반응식

HRID 2233938 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10]C2C(F)=C(F)C(F)=C(F)C=2F)=O)[NH:5][C:6]=1[CH3:7].Cl.[NH2:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:31]=[C:32]([CH:37]=[C:38]([Cl:40])[N:39]=2)[C:33]([O:35][CH3:36])=[O:34])[CH2:26][CH2:25]1>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:23][CH:24]2[CH2:25][CH2:26][N:27]([C:30]3[CH:31]=[C:32]([CH:37]=[C:38]([Cl:40])[N:39]=3)[C:33]([O:35][CH3:36])=[O:34])[CH2:28][CH2:29]2)=[O:10])[NH:5][C:6]=1[CH3:7]

참가 물질

4

반응물 2

HCID 86608241Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate2회HCID 86608260Methyl 2-(4-aminopiperidin-1-yl)-6-chloroisonicotinate hydrochloride salt2회

생성물 1

HCID 86608287Methyl 2-(4-{[(4-bromo-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-chloroisonicotinate수율 76.1%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate (intermediate 17, 1.81 g, 4.90 mmol) and TEA (682 μl, 4.9 mmol) were added to methyl 2-(4-aminopiperidin-1-yl)-6-chloroisonicotinate hydrochloride salt (Intermediate 93; 1.5 g, 4.90 mmol) in anhydrous DMA (10 ml). The mixture was stirred at room temperature 18 h then partitioned between EtOAc and water. The organic layer was washed with water, dried over Na2SO4 and concentrated under vacuum. The solid material was purified by flash chromatography eluting with EtOAc/n-hexanes mixture (7:3) to give the title compound as a brown solid (1.7 g).

후처리

  1. customthen partitioned between EtOAc and water
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe solid material was purified by flash chromatography
  6. washeluting with EtOAc/n-hexanes mixture (7:3)

출처 및 근거

ORD 기록
ord-beee9fc68d4e46b4b3a3e740a012238d
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709503B2

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