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 2233938ノート

反応式

HRID 2233938 の反応式
[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]

参加物

4

反応物 2

HCID 86608241Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate2 回HCID 86608260Methyl 2-(4-aminopiperidin-1-yl)-6-chloroisonicotinate hydrochloride salt2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-beee9fc68d4e46b4b3a3e740a012238d
出典データセット
uspto-grants-2010_05
特許番号
US07709503B2

反応ノート

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