3-Pyridinemethanamine → HCID 46883208, compound

HRID 2272935Notes

Reaction equation

HRID 2272935 reaction equation
Cl[C:2]1[N:3]=[C:4]([C:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[O:13])[C:5]2[S:10][C:9]([Cl:11])=[CH:8][C:6]=2[N:7]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][NH2:26])[CH:20]=1>C(O)CCC>[Cl:11][C:9]1[S:10][C:5]2[C:4]([C:12]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[O:13])=[N:3][C:2]([NH:26][CH2:25][C:21]3[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=3)=[N:7][C:6]=2[CH:8]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 58270231HCID 58270231, compound

Product 1

HCID 46883208HCID 46883208, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

A stirred solution of Example 4 (5 g, 16 mmol) in n-butanol (120 ml) was treated with 3-picolylamine (8.1 ml, 80 mmol) and heated to 100° C. for 2 h. The reaction mixture was cooled to room temperature, reduced in vacuo and the residue purified by silica gel (100 g) column chromatography (3% MeOH/DCM) affording the title compound in 38% yield, >95% purity. LC-MS m/z=387.0 [M+H]+; RT=3.30 min; LC-MS method 1.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe residue purified by silica gel (100 g) column chromatography (3% MeOH/DCM)

Sources & evidence

ORD record
ord-6c3d9fc1f4d84785ba2748d009a4582e
Source dataset
uspto-grants-2015_09
Patent number
US09120807B2

Reaction notes

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