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2-Pyridinemethanamine → 6-Amino-4-furan-2-yl-2-[(pyridin-2-ylmethyl)-amino]-nicotinonitrile

HRID 1356068
Notes
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Reaction equation

HRID 1356068 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:5]([C:6]#[N:7])=[C:4](S(C)=O)[N:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][NH2:25]>COCCOC>[NH2:1][C:2]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:5]([C:6]#[N:7])=[C:4]([NH:25][CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 185075486-Amino-4-furan-2-yl-2-methanesulfinyl-nicotinonitrile

Product 1

HCID 185074196-Amino-4-furan-2-yl-2-[(pyridin-2-ylmethyl)-amino]-nicotinonitrileYield 34%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of 250 mg (1.01 mmol) 6-amino-4-furan-2-yl-2-methanesulfinyl-nicotinonitrile in 10 ml DME was added 0.41 ml (4.04 mmol) 2-picolylamine and the mixture heated at 100° C. for 16 hours. The reaction mixture was then cooled to room temperature and partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate) followed by trituration in ether afforded 100 mg (34%) 6-amino-4-furan-2-yl-2-[(pyridin-2-ylmethyl)-amino]-nicotinonitrile as an off-white crystalline solid. ES-MS m/e (%): 292 (M+H+, 100).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. custompartitioned between water and dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-482e654629cd42d383865bbe32db4136
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06586441B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes