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Water → cis-(1-(6-Amino-5-nitropyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone

HRID 931326
Notes
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Reaction equation

HRID 931326 reaction equation
Cl.[CH3:2][C@H:3]1[NH:8][CH2:7][C@@H:6]([C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:24]1[N:29]=[C:28]([NH2:30])[C:27]([N+:31]([O-:33])=[O:32])=[CH:26][CH:25]=1.O>C(#N)C>[NH2:30][C:28]1[N:29]=[C:24]([N:8]2[C@H:3]([CH3:2])[CH2:4][CH2:5][C@H:6]([C:9]([N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[O:10])[CH2:7]2)[CH:25]=[CH:26][C:27]=1[N+:31]([O-:33])=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 89853697cis-(6-Methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone hydrochloride

Product 1

HCID 89853803cis-(1-(6-Amino-5-nitropyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanoneYield 100%

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent

Procedure

To a solution of cis-(6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone hydrochloride (0.5 g, 2.15 mmol) in acetonitrile (10 mL) was added triethylamine (0.89 mL, 6.46 mmol). The mixture was stirred at room temperature for 10 min. Then 6-chloro-3-nitropyridin-2-amine (260 mg, 1.50 mmol) was added and the reaction mixture was stirred at 80° C. for 3 h and then at room temperature for 12 h. Water was added and the mixture was extracted with ethyl acetate. The organics were dried over sodium sulfate and concentrated under reduced pressure to afford cis-(1-(6-amino-5-nitropyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone (0.5 g). MS (ES+APCI) (M+H) 334.2; LCMS retention time 4.028 min (Method S1).

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for 3 h
  2. waitat room temperature for 12 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-590f7c20874344d98a0c4bfed1ca5a77
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