HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

[3-(6-Nitro-pyridin-3-yl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester → [3-(6-Amino-pyridin-3-yl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester

HRID 1850608
Notes
Print preview

Reaction equation

HRID 1850608 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]12[CH2:13][CH:12]1[CH2:11][N:10]([C:14]1[CH:15]=[N:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=1)[CH2:9]2)([CH3:4])([CH3:3])[CH3:2]>CO.C(Cl)Cl.C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]12[CH2:13][CH:12]1[CH2:11][N:10]([C:14]1[CH:15]=[N:16][C:17]([NH2:20])=[CH:18][CH:19]=1)[CH2:9]2)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 67357051[3-(6-Nitro-pyridin-3-yl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester

Product 1

HCID 67355528[3-(6-Amino-pyridin-3-yl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl esterYield 88.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent
HCID 21226129
Dichloromethane methanol
Solvent

Procedure

To a solution of [3-(6-Nitro-pyridin-3-yl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester (150 mg, 0.468 mmol) in MeOH—CH2Cl2 (3:1) was added Pd/C (24.92 mg, 0.234 mmol). The resulting mixture was stirred under H2 balloon (H2/vacuum exchange three times) at r.t. for 4 h. LCMS showed complete conversion. The reaction mixture was then filtered through a pad of Celite with DCM and concentrated to give a black precipitate. This precipitate was diluted in ethyl acetate followed by filtration. The filtrate was then evaporated to give 120 mg of [3-(6-Amino-pyridin-3-yl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester in 88% yield. MS (ESI) m/e (M+H+): 291.1

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of Celite with DCM
  2. concentrationconcentrated
  3. customto give a black precipitate
  4. filtrationfollowed by filtration
  5. customThe filtrate was then evaporated

Sources & evidence

ORD record
ord-ae3a94209be546098fc192c1384f1944
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957074B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes