Thionyl Chloride → 7-bromo-N-(5-(2-(2,6-cis-dimethylpiperidin-1-yl)ethylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 335330

反応式

HRID 335330 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=3[F:23])[C:17](O)=[O:18])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.S(Cl)(Cl)=O.NC1C=C(C=CC=1F)C([NH:34][CH2:35][CH2:36][N:37]1[C@H:42]([CH3:43])[CH2:41][CH2:40][CH2:39][C@@H:38]1[CH3:44])=O>C1(C)C=CC=CC=1.N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:15]=[C:16]([C:17](=[O:18])[NH:34][CH2:35][CH2:36][N:37]4[C@H:42]([CH3:43])[CH2:41][CH2:40][CH2:39][C@@H:38]4[CH3:44])[CH:20]=[CH:21][C:22]=3[F:23])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1

参加物

6

反応物 3

HCID 24386Thionyl ChlorideHCID 712834433-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluorobenzoic acid2 回HCID 866956853-Amino-N-(2-(2,6-cis-dimethylpiperidin-1-yl)ethyl)-4-fluorobenzamide

生成物 1

HCID 712832197-bromo-N-(5-(2-(2,6-cis-dimethylpiperidin-1-yl)ethylcarbamoyl)-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 1140Toluene溶媒

実験手順

7-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid (Intermediate 1A step 3) (1.150 g, 4.77 mmol) was suspended in toluene (10 ml) and treated with thionyl chloride (1.045 ml, 14.32 mmol). The mixture was at 100° C. for 2 hrs. The solvent was removed in vacuo and the solid was added to a stirred solution of 3-amino-N-(2-(2,6-cis-dimethyl piperidin-1-yl)ethyl)-4-fluorobenzamide (1.4 g, 4.77 mmol) in dry pyridine (5 ml) containing oven dried molecular sieves. The mixture was stirred at RT under nitrogen atmosphere overnight. The solvent was removed in vacuo and purification of the crude product by chromatography on silica eluting with 0-20% MeOH in DCM afforded the title compound;

後処理

  1. customThe solvent was removed in vacuo
  2. additioncontaining oven
  3. customdried molecular sieves
  4. customThe solvent was removed in vacuo and purification of the crude product by chromatography on silica eluting with 0-20% MeOH in DCM

出典と根拠

ORDレコード
ord-0a91ea3831a342029be8335cf83b358a
出典データセット
uspto-grants-2014_11
特許番号
US08883819B2

関連ノート

読み込み中…