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Oxalyl chloride → (E)-4-Methyl-1-[(1S,4S)-5-(2-methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pent-2-en-1-one

HRID 1775343
Notes
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Reaction equation

HRID 1775343 reaction equation
[CH3:1][CH:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:16][C:17]1[C:22]([N:23]2[CH2:28][C@@H:27]3[CH2:29][C@H:24]2[CH2:25][NH:26]3)=[CH:21][CH:20]=[CH:19][N:18]=1.CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C>[CH3:8][CH:2]([CH3:1])/[CH:3]=[CH:4]/[C:5]([N:26]1[CH2:25][C@@H:24]2[CH2:29][C@H:27]1[CH2:28][N:23]2[C:22]1[C:17]([CH3:16])=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 6420393-Isopropyl acrylic acidHCID 89825789(1S,4S)-5-(2-Methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane hydrochloride

Product 1

HCID 89833044(E)-4-Methyl-1-[(1S,4S)-5-(2-methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pent-2-en-1-oneYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(E)-4-Methylpent-2-enoic acid (57 mg, 0.5 mmol) was dissolved in dichloromethane (2 ml), oxalyl chloride (42 μl, 0.5 mmol) and one drop of DMF were added and the resulting solution was stirred at room temperature for 15 minutes. This solution was added to a solution of (1S,4S)-5-(2-methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane hydrochloride (66 mg, 0.3 mmol) in DCM (2 ml). DIPEA (175 μl, 1 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 59 mg of a solid (0.21 mmol, 69%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and acetonitrile)

Sources & evidence

ORD record
ord-e86a41553aad451bb37bb53a37198cbb
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260441B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes