Hydrochloric Acid → N-(2-(4-chlorophenyl)ethyl)-3-hydroxypyridine-2-Carboxamide

HRID 584723ノート

反応式

HRID 584723 の反応式
F[C:2](F)(F)[C:3]1[CH:16]=[CH:15][C:6](OC2C=CC(N)=CC=2)=[CH:5][CH:4]=1.Br[C:20]1[N:25]=[C:24]([C:26](Cl)=[O:27])[C:23]([O:29]CC2C=CC=CC=2)=[C:22](OC)[CH:21]=1.[ClH:39].C([N:42]([CH2:45]C)CC)C.[H][H]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O.[Pd]>[Cl:39][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][CH2:45][NH:42][C:26]([C:24]2[C:23]([OH:29])=[CH:22][CH:21]=[CH:20][N:25]=2)=[O:27])=[CH:16][CH:15]=1

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27607514-(4-(Trifluoromethyl)phenoxy)anilineHCID 221750736-bromo-3-benzyloxy-4-methoxypyridine-2-carbonyl ChlorideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 22175087N-(2-(4-chlorophenyl)ethyl)-3-hydroxypyridine-2-Carboxamide

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 23938Palladium触媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 4-(4-trifluoromethylphenoxy)aniline (0.20 g, 0.8 mmol) and DMAP (0.10 g, 0.085 mmol) in CH2Cl2 (10 mL) was added all at once a solution of 3-benzyloxy-6-bromo-4-methoxypyridin-2-carbonylchloride (3) (0.29 g, 0.8 mmol) in CH2Cl2 (5 mL). The resulting mixture was stirred overnight at room temperature then poured into 2N HCl (10 mL). The organic layer was separated and the aqueous layer extracted with CH2Cl2 (2×10 mL). The organic layers were combined, dried (MgSO4) and concentrated to give a gummy solid. This solid was taken up in EtOAc (20 mL), and triethylamine (0.80 g, 0.8 mmol) and 5% Pd on carbon (0.10 g) were added. The resulting mixture was subjected to a hydrogen atmosphere (initial pressure=50 psi) on a Parr shaker for 30 minutes. The mixture was filtered, washed with 0.1N HCl (20 mL), dried (MgSO4) and concentrated to give the title compound as an off-white solid (0.14 g), m.p.=122-129° C. Coupling Procedure C: Preparation of N-(4-Cyclohexylphenyl)-3-hydroxypyridine-2-carboxamide.

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with CH2Cl2 (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a gummy solid
  6. customfor 30 minutes
  7. filtrationThe mixture was filtered
  8. washwashed with 0.1N HCl (20 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-26989112bbae4c98a2b758c4ef471153
出典データセット
uspto-grants-2005_08
特許番号
US06927225B2

反応ノート

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