Tributylamine → 5'-Chloro-3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-carboxylic acid [4-(3-dimethylamino-pyrrolidin-1-yl)phenyl]amid

HRID 2426698Notes

Reaction equation

HRID 2426698 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][C:28]([Cl:31])=[CH:27][N:26]=1.C(N(CCCC)CCCC)CCC>>[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][C:28]([Cl:31])=[CH:27][N:26]=4)[CH2:19][CH2:18]3)=[O:16])=[CH:12][CH:13]=2)[CH2:4]1

Participants

4

Reactant 3

HCID 7622TributylamineHCID 276852,5-DichloropyridineHCID 67147939Piperidine-4-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Product 1

HCID 588665985'-Chloro-3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-carboxylic acid [4-(3-dimethylamino-pyrrolidin-1-yl)phenyl]amid

Procedure

Piperidine-4-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide (30 mg), 2,5-dichloropyridine (30 mg) and tributylamine (0.2 ml) were heated at 160° C. for 2 hours. The cooled crude mixture was washed with heptane and purified by chromatography (silica gel, eluent: ethyl acetate/ammonia (3N in methanol)). This resulted in the product with the molecular weight of 427.98 (C23H30CIN5O); MS (ESI): 428 (M+H+).

Workup

  1. temperatureThe cooled crude mixture
  2. washwas washed with heptane
  3. custompurified by chromatography (silica gel, eluent: ethyl acetate/ammonia (3N in methanol))
  4. customThis resulted in the product with the molecular weight of 427.98 (C23H30CIN5O)

Sources & evidence

ORD record
ord-c3805d6ba2c54e44a954c1fc31145d86
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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