Pyridine → 4-Fluoro-N-[2-methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl]-benzenesulfonamide

HRID 536320

反応式

HRID 536320 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.[F:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.C(O)C(N)(CO)CO>ClCCCl>[F:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([N:9]3[CH2:13][CH2:12][C@@H:11]([N:14]4[CH2:18][CH2:17][CH2:16][C@@H:15]4[CH3:19])[CH2:10]3)=[CH:5][CH:6]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 95884-Fluorobenzenesulfonyl chlorideHCID 674804612-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]pyridin-3-amine

生成物 1

HCID 545971574-Fluoro-N-[2-methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl]-benzenesulfonamide収率 18.3%

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 4-fluoro-benzenesulfonyl chloride (53 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 6.9 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-6e70391e63db482a90bcbb12d4d30b5d
出典データセット
uspto-grants-2014_10
特許番号
US08859588B2

関連ノート

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