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Diisopropylethylamine → 3,6-Dichloro-5-[4-(1-isopropoxycarbonyl-piperidin-4-yloxyimino)-piperidin-1-yl]-pyrazine-2-carboxylic acid methyl ester

HRID 2066870
Notes
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Reaction equation

HRID 2066870 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[N:7][O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.[CH3:21][O:22][C:23]([C:25]1[C:30]([Cl:31])=[N:29][C:28](Cl)=[C:27]([Cl:33])[N:26]=1)=[O:24].C(N(C(C)C)CC)(C)C>CS(C)=O.C([O-])(O)=O.[Na+]>[CH3:21][O:22][C:23]([C:25]1[C:30]([Cl:31])=[N:29][C:28]([N:1]2[CH2:2][CH2:3][C:4](=[N:7][O:8][CH:9]3[CH2:10][CH2:11][N:12]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]3)[CH2:5][CH2:6]2)=[C:27]([Cl:33])[N:26]=1)=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 152582053,5,6-Trichloro-pyrazine-2-carboxylic acid methyl esterHCID 57461147Isopropyl 4-(Piperidin-4-ylideneaminooxy)piperidine-1-carboxylate

Product 1

HCID 866550133,6-Dichloro-5-[4-(1-isopropoxycarbonyl-piperidin-4-yloxyimino)-piperidin-1-yl]-pyrazine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 516892Sodium BicarbonateSolvent

Procedure

2d (99 mg, 0.35 mmol), 56a (92 mg, 0.35 mmol) and diisopropylethylamine (0.1 mL, 0.6 mmol) were combined in 0.5 mL of DMSO and stirred at room temperature for 18 h. The mixture was diluted with aqueous NaHCO3 (5 mL) and extracted with EtOAc (5 mL). The organic layer was concentrated under vacuum to afford the crude 56b. 20 mg of this crude material was purified by preparative HPLC to afford 56b: LC-MS 488.3 (MH+).

Workup

  1. extractionextracted with EtOAc (5 mL)
  2. concentrationThe organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-d69272d16ad240e8a6b48eb2e1805719
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293729B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes