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3-Pyridinemethanamine → 7-(dibenzylamino)-N-(3-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

HRID 1821843
Notes
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Reaction equation

HRID 1821843 reaction equation
[CH2:1]([N:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([C:18]([O:20]CC)=O)[NH:15][C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:30][CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1>ClCCl.O>[CH2:23]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([C:18]([NH:30][CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[O:20])[NH:15][C:14]=12)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 310183-PyridinemethanamineHCID 68982508HCID 68982508, compound

Product 1

HCID 578935047-(dibenzylamino)-N-(3-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamideYield 49.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (Reference Example 3) (634 mg, 1.64 mmol) and 3-(aminomethyl)pyridine (3.8 mL, 37 mmol) was heated neat at 100° C. for 72 h under N2. The mixture was cooled to room temperature and diluted with dichloromethane (150 mL) and water (100 mL). The layers were separated, and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by chromatography (silica gel, gradient 50-70% ethyl acetate/hexanes) to provide 7-(dibenzylamino)-N-(3-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (364 mg, 49%) as an orange solid: Rf 0.08 (75:25 ethyl acetate/hexanes); mp 105-108° C.; 1H NMR (300 MHz, CDCl3) δ4.60 (2H, d, J=6.0 Hz), 4.89 (4H, s), 6.50 (1H, t, J=5.4 Hz), 6.71 (1H, s), 6.99 (1H, d, J=5.6 Hz), 7.28-7.31 (2H, m), 7.34-7.42 (9H, m), 7.64 (1H, d, J=7.8 Hz), 7.89 (1H, d, J=5.6 Hz), 8.55 (2H, s), 8.97 (1H, s); ESI MS m/z 448 [C28H25N5O+H]+; HPLC (Method A) >99% (AUC), tR=13.02 min.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (2×50 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (silica gel, gradient 50-70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-244fda1d82164e7b9b323a03a1fe80da
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07608627B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes