3-Pyridinemethanamine → HCID 22283234, compound

HRID 2250720Notes

Reaction equation

HRID 2250720 reaction equation
Cl[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=2[N:6]=1.[NH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>O1CCOCC1>[CH3:18][O:17][C:7]1[C:5]2[N:6]=[C:2]([NH:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[S:3][C:4]=2[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 22283210HCID 22283210, compound

Product 1

HCID 22283234HCID 22283234, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-chloro-4-methoxy-7-phenyl-benzothiazole (150 mg, 0.54 mmol), in dioxane (5 ml) was added 3-(aminomethyl)-pyridine (176 mg, 1.6 mmol) and this mixture was stirred at 100° C. for 18 h. The solvent was then evaporated and the mixture taken up in methanol (8 ml) and ultrasonnicated for 10 min. to precipitate the product, which was washed with methanol (5 ml), and dried under vacuum (0.05 mmHg, 60° C.) to afford the title compound as a white solid (58 mg, 31% yield), MS: m/e=348.3 (M+H+).

Workup

  1. customThe solvent was then evaporated
  2. waitthe mixture taken up in methanol (8 ml) and ultrasonnicated for 10 min.
  3. customto precipitate the product, which
  4. washwas washed with methanol (5 ml)
  5. customdried under vacuum (0.05 mmHg, 60° C.)

Sources & evidence

ORD record
ord-1de8833696fe4bbca68a7759fba90286
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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