2-Chloropyridine → HCID 58867535, compound

HRID 2426697Notes

Reaction equation

HRID 2426697 reaction equation
[CH3:1][N:2]([CH3:23])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[O:16])=[CH:10][CH:9]=2)[CH2:4]1.Cl[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1>>[CH3:1][N:2]([CH3:23])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]([CH:17]3[CH2:22][CH2:21][N:20]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH2:19][CH2:18]3)=[O:16])=[CH:12][CH:13]=2)[CH2:4]1

Participants

3

Reactant 2

HCID 79772-Chloropyridine2×HCID 67147939Piperidine-4-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Product 1

HCID 58867535HCID 58867535, compound

Conditions

Temperature
160 °C

Procedure

Piperidine-4-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]-amide (30 mg) and 2-chloropyridine (90 mg) were heated at 160° C. for 2 hours. 2-Chloropyridine (0.2 ml) was added and the mixture was again heated at 160° C. for 4 hours. The cooled crude mixture was purified by chromatography (silica gel, eluent: ethyl acetate/ammonia (3N in methanol)). This resulted in the product with the molecular weight of 393.54 (C23H31N5O); MS (ESI): 394 (M+H+).

Workup

  1. temperatureThe cooled crude mixture
  2. customwas purified by chromatography (silica gel, eluent: ethyl acetate/ammonia (3N in methanol))
  3. customThis resulted in the product with the molecular weight of 393.54 (C23H31N5O)

Sources & evidence

ORD record
ord-d009e684e9cc4f0487e9fe490228f78c
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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