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

반응식

HRID 335330 반응식
[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

참가 물질

6

반응물 3

HCID 24386Thionyl ChlorideHCID 712834433-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluorobenzoic acid2회HCID 866956853-Amino-N-(2-(2,6-cis-dimethylpiperidin-1-yl)ethyl)-4-fluorobenzamide

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 1140Toluene용매

실험 절차

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;

후처리

  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

출처 및 근거

ORD 기록
ord-0a91ea3831a342029be8335cf83b358a
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883819B2

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