Pyridine → 3,5-Dimethyl-isoxazole-4-carboxylic acid [2-methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl]-amide

HRID 536319

反応式

HRID 536319 の反応式
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([N:9]2[CH2:13][CH2:12][C@@H:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[CH2:10]2)[N:3]=1.N1C=CC=CC=1.[CH3:26][C:27]1[C:31]([C:32](Cl)=[O:33])=[C:30]([CH3:35])[O:29][N:28]=1.C(O)C(N)(CO)CO>ClCCCl>[CH3:1][C:2]1[C:7]([NH:8][C:32]([C:31]2[C:27]([CH3:26])=[N:28][O:29][C:30]=2[CH3:35])=[O:33])=[CH:6][CH:5]=[C:4]([N:9]2[CH2:13][CH2:12][C@@H:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[CH2:10]2)[N:3]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 27362653,5-Dimethylisoxazole-4-carbonyl ChlorideHCID 674804612-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]pyridin-3-amine

生成物 1

HCID 545971563,5-Dimethyl-isoxazole-4-carboxylic acid [2-methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl]-amide収率 35.9%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

To a solution of 2-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]pyridin-3-amine (22.7 mg, 0.09 mmol) in DCE (1 mL) was added pyridine (0.22 mL, 2.7 mmol) followed by a solution of 3,5-dimethyl-isoxazole-4-carbonyl chloride (43 mg, 0.27 mmol) in DCE (1 mL) and stirred at ambient temperature for 5 hours. To this mixture was then added trisamine resin (200 mg, 0.8 mmol, 4 mmol/g loading), stirred for 30 min, filtered and concentrated to afford a crude solid which was purified by flash column chromatography (5% 7N NH3 in MeOH/CH2Cl2) to obtain 12.4 mg of the title compound.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto afford a crude solid which
  4. customwas purified by flash column chromatography (5% 7N NH3 in MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-df017cd31ca74dc7a4ea446d02557373
出典データセット
uspto-grants-2014_10
特許番号
US08859588B2

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