2,6-Lutidine → 4-tert-butyl-N-[5-chloro-2-(4-methyl-5-piperidin-4-yl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-benzenesulfonamide

HRID 2245841ノート

反応式

HRID 2245841 の反応式
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=O)[NH:18][CH3:19])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:23].N1C(C)=CC=CC=1C.[C:34]([C:38]1[CH:43]=[CH:42][C:41]([S:44]([NH:47][C:48]2[C:49]([C:55]([NH:57][NH2:58])=O)=[N:50][C:51](Cl)=[CH:52][CH:53]=2)(=[O:46])=[O:45])=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35].CCN(C(C)C)C(C)C>O1CCOCC1.CC#N>[C:34]([C:38]1[CH:39]=[CH:40][C:41]([S:44]([NH:47][C:48]2[C:49]([C:55]3[N:18]([CH3:19])[C:17]([CH:14]4[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]4)=[N:58][N:57]=3)=[N:50][CH:51]=[C:52]([Cl:23])[CH:53]=2)(=[O:45])=[O:46])=[CH:42][CH:43]=1)([CH3:37])([CH3:36])[CH3:35]

参加物

8

反応物 5

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 59216825Benzyl 4-(N-methylcarbamoyl)piperidine-1-carboxylateHCID 866183534-tert-butyl-N-(6-chloro-2-hydrazinocarbonyl-pyridin-3-yl)-benzenesulfonamide

生成物 1

HCID 248044394-tert-butyl-N-[5-chloro-2-(4-methyl-5-piperidin-4-yl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-benzenesulfonamide

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
40 °C

実験手順

A 25 mL scintillation vial was charged with 4-methylcarbamoyl-piperidine-1-carboxylic acid benzyl ester (138 mg, 0.5 mmol), POCl3 (0.095 mL, 1.0 mmol), 2,6-lutidine (130 mg, 1.25 mmol), and CH3CN (1.5 mL). The vial was sealed, heated to 40° C., and stirred for four hours. The volatiles were then evacuated in vacuo and to the resultant residue was added 4-tert-butyl-N-(6-chloro-2-hydrazinocarbonyl-pyridin-3-yl)-benzenesulfonamide (193 mg, 0.5 mmol), DIPEA (0.5 mL), and dioxane (1.0 mL). The vial was sealed, heated to 130° C., and stirred for two hours. The volatiles were then removed in vacuo and to the residue was added 3 mL of 33% hydrobromic acid in acetic acid. The vial was sealed and stirred for 3 h. The volatiles were then evacuated in vacuo and the residue was purified via preparatory HPLC to afford 4-tert-butyl-N-[5-chloro-2-(4-methyl-5-piperidin-4-yl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-benzenesulfonamide as a white powder: MS (ES) M+H expected 489.2, found 488.5.

後処理

  1. customThe vial was sealed
  2. customThe volatiles were then evacuated in vacuo and to the resultant residue
  3. customThe vial was sealed
  4. temperatureheated to 130° C.
  5. stirringstirred for two hours
  6. customThe volatiles were then removed in vacuo and to the residue
  7. additionwas added 3 mL of 33% hydrobromic acid in acetic acid
  8. customThe vial was sealed
  9. stirringstirred for 3 h
  10. customThe volatiles were then evacuated in vacuo
  11. customthe residue was purified via preparatory HPLC

出典と根拠

ORDレコード
ord-6e43098ede8a4fd6b944eb3eb97cdeb3
出典データセット
uspto-grants-2010_03
特許番号
US07683176B2

反応ノート

読み込み中…