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Triethylamine → 6-(3-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)piperidin-1-yl)-3-nitropyridin-2-amine

HRID 931130
Notes
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Reaction equation

HRID 931130 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[N:8]3[CH2:14][CH2:13][CH2:12][C:9]3=[N:10][N:11]=2)[CH2:2]1.Cl[C:16]1[N:21]=[C:20]([NH2:22])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][CH:17]=1.C(N(CC)CC)C>C(#N)C>[N:10]1[N:11]=[C:7]([CH:3]2[CH2:4][CH2:5][CH2:6][N:1]([C:16]3[N:21]=[C:20]([NH2:22])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][CH:17]=3)[CH2:2]2)[N:8]2[CH2:14][CH2:13][CH2:12][C:9]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 431427873-{5H,6H,7H-pyrrolo[2,1-c][1,2,4]triazol-3-yl}piperidine

Product 1

HCID 898542026-(3-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)piperidin-1-yl)-3-nitropyridin-2-amineYield 72.3%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

To a solution of 3-(piperidin-3-yl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole (900 mg, 4.68 mmol) in acetonitrile (50 mL) was added 6-chloro-3-nitropyridin-2-amine (730 mg, 4.2 mmol) and triethylamine (1.42 g, 14.04 mmol) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for 30 min at reflux, then allowed to cool down to room temperature and stirred for 16 h. The solvent was removed under reduced pressure and the resulting residue was partitioned between water and ethyl acetate. The organics were dried over sodium sulfate, concentrated under reduced pressure and purified via column chromatography to afford the title compound (1.0 g, 64.9%). MS (ES+) (M+H) 330.33; LCMS retention time: 2.85 min (Method S).

Workup

  1. temperatureat reflux
  2. stirringstirred for 16 h
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting residue was partitioned between water and ethyl acetate
  5. dry with materialThe organics were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified via column chromatography

Sources & evidence

ORD record
ord-14430e84c40142d799295a3f557a8982
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296745B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes