2-Pyridinemethanamine → HCID 59487297, compound

HRID 1925554Notes

Reaction equation

HRID 1925554 reaction equation
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][NH2:39].[F:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][CH2:49][S:50][C:51]2[N:59]=[CH:58][CH:57]=[CH:56][C:52]=2[C:53](O)=[O:54])=[CH:43][CH:42]=1>C(Cl)Cl.CCCCCC.CC(=O)OCC>[F:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][CH2:49][S:50][C:51]2[C:52]([C:53]([NH:39][CH2:38][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=3)=[O:54])=[CH:56][CH:57]=[CH:58][N:59]=2)=[CH:43][CH:42]=1

Participants

8

Reactant 5

HCID 195092-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67133585HCID 67133585, compound

Product 1

HCID 59487297HCID 59487297, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

520 mg (2.74 mmol) of EDC hydrochloride, 250 mg (1.64 mmol) of HOBT, 0.9 ml (5.48 mmol) of DIPEA and 180 mg (1.64 mmol) of pyridin-2-yl-methanamine were added in succession to a solution of 400 mg (1.37 mmol) of 2-(3-(4-fluorophenyl)-propylthio)nicotinic acid in DCM (6 ml), and the mixture was stirred for 4 h at RT. Dilution with water (40 ml) and extraction with DCM (3×50 ml) were then carried out. The combined organic phases were washed with a sat. NH4Cl sol. and water, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 22:3) of the residue yielded 240 mg (0.63 mmol, 46%) of 2-[3-(4-fluorophenyl)-propylsulfanyl]-N-(pyridin-2-yl-methyl)-pyridine-3-carboxylic acid amide. MS: m/z 382.1 [M+H]+.

Workup

  1. extractionDilution with water (40 ml) and extraction with DCM (3×50 ml)
  2. washThe combined organic phases were washed with a sat. NH4Cl sol. and water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a43110cb7f5a4179ac3333c1f1e07595
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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