1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3,5-Dimethyl-isoxazole-4-carboxylic acid [4-chloro-5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

HRID 1774859ノート

反応式

HRID 1774859 の反応式
Cl.[NH2:2][CH2:3][C:4]1[C:5]([Cl:22])=[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13]3)[CH:7]=[N:8][CH:9]=1.CCN=C=NCCCN(C)C.OC1C2N=NNC=2C=CC=1.CCN(C(C)C)C(C)C.[CH3:53][C:54]1[C:58]([C:59](O)=[O:60])=[C:57]([CH3:62])[O:56][N:55]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[Cl:22][C:5]1[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13]3)=[CH:7][N:8]=[CH:9][C:4]=1[CH2:3][NH:2][C:59]([C:58]1[C:54]([CH3:53])=[N:55][O:56][C:57]=1[CH3:62])=[O:60]

参加物

9

反応物 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 756363,5-Dimethylisoxazole-4-carboxylic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 866792006-(5-Aminomethyl-4-chloro-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochlorideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 866792023,5-Dimethyl-isoxazole-4-carboxylic acid [4-chloro-5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide収率 48%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-(5-aminomethyl-4-chloro-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride (example 218, 0.05 g, 0.148 mmol) in dry DMF (1 mL) were added EDCI (0.034 g, 0.077 mmol), hydroxybenzotriazole (0.017 g, 0.077 mmol), Hünig's base (0.057 g, 0.443 mmol) and 3,5-dimethyl-isoxazole-4-carboxylic acid (0.021 g, 0.148 mmol) and the resulting solution was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc, poured into sat. NaHCO3 solution (10 mL) and extracted with EtOAc (2×20 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.03 g, 48%) as a colorless solid. MS: 425.4 (M+H+).

後処理

  1. extractionextracted with EtOAc (2×20 mL)
  2. dry with materialCombined organics were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluting with a 0 to 5% MeOH-DCM gradient

出典と根拠

ORDレコード
ord-14236c5db8b24e8283b2ac4e2a664f9f
出典データセット
uspto-grants-2016_02
特許番号
US09260408B2

反応ノート

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