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

HRID 1521344Notes

Reaction equation

HRID 1521344 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=[C:4]2[CH:3]=1.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:20]=[C:21]([CH:35]=[CH:36][C:37]=1[F:38])[C:22]([NH:24][CH2:25][CH2:26][N:27]1[C@H:32]([CH3:33])[CH2:31][CH2:30][CH2:29][C@@H:28]1[CH3:34])=[O:23]>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:18][C:19]3[CH:20]=[C:21]([C:22](=[O:23])[NH:24][CH2:25][CH2:26][N:27]4[C@H:32]([CH3:33])[CH2:31][CH2:30][CH2:29][C@@H:28]4[CH3:34])[CH:35]=[CH:36][C:37]=3[F:38])=[O:13])=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 672614887-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid2×HCID 866956853-Amino-N-(2-(2,6-cis-dimethylpiperidin-1-yl)ethyl)-4-fluorobenzamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

7-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid (Intermediate 1) (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;

Workup

  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

Sources & evidence

ORD record
ord-920aa7ab4e414abdb4cd0e860bfc74fe
Source dataset
uspto-grants-2015_07
Patent number
US09073921B2

Reaction notes

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