Pyridine → 6-Bromo-N-(2-methyl-5-(2-(4-methylpiperazin-1-yl)benzylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxamide

HRID 335325

Reaction equation

HRID 335325 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([OH:13])=O)[CH:7]=1.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:20]=[C:21]([CH:39]=[CH:40][C:41]=1[CH3:42])[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]1)=[O:23].N1C=CC=CC=1>CO.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([NH:18][C:19]2[CH:20]=[C:21]([C:22](=[O:23])[NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:32]3[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]3)[CH:39]=[CH:40][C:41]=2[CH3:42])=[O:13])[CH:7]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 573723196-Bromopyrazolo(1,5-a)pyridine-3-carboxylic acidHCID 866956843-Amino-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide

Product 1

HCID 712832536-Bromo-N-(2-methyl-5-(2-(4-methylpiperazin-1-yl)benzylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture comprising 6-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid (commercially available) (196 mg, 0.813 mmol) and thionyl chloride (2 ml, 27.4 mmol) was heated at 60° C. for 1 hr and concentrated in vacuo. To this was added 3-amino-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide (step 1) (220 mg, 0.651 mmol) and pyridine (5 ml). The reaction was stirred under nitrogen at room temperature for 2 hrs. The mixture was diluted with 10% MeOH in EtOAc and washed with water, sat NaHCO3, brine and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/DCM to afford the title compound;

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with water
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/DCM

Sources & evidence

ORD record
ord-597139d1a1e7458c803747dda0be57a9
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Linked notes

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