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Citric Acid → HCID 178483292, compound

HRID 1480438
Notes
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Reaction equation

HRID 1480438 reaction equation
[C:1](Cl)(=[O:13])[O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[C:6]([Cl:12])[CH:5]=1.[CH3:15][N:16]([CH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:17]([C:19]1[N:20]=[N:21][NH:22][CH:23]=1)=[O:18].C(=O)(O)[O-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH3:15][N:16]([CH2:24][CH2:25][CH:26]1[CH2:27][CH2:28][N:29]([C:1]([O:2][CH2:3][C:4]2[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[C:6]([Cl:12])[CH:5]=2)=[O:13])[CH2:30][CH2:31]1)[C:17]([C:19]1[N:20]=[N:21][NH:22][CH:23]=1)=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 311Citric AcidHCID 516892Sodium BicarbonateHCID 86722663HCID 86722663, compoundHCID 178483276HCID 178483276, compound

Product 1

HCID 178483292HCID 178483292, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To 3-chloro-5-cyanobenzyl carbonochloridate (step 4) (65.5 mg, 0.285 mmol) and N-methyl-N-(2-(piperidin-4-yl)ethyl)-1H-1,2,3-triazole-4-carboxamide (step 3) (78 mg, 0.285 mmol) in DCM (5 mL) was added saturated aqueous sodium bicarbonate solution (5 mL, 0.285 mmol), and the mixture stirred vigorously for 16 hrs. The resulting mixture was acidified with 10% citric acid solution and the organic portion was separated, dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in DCM and applied to a 12 g silica cartridge eluting with 0-100% EtOAc/iso-hexane. The product fractions were combined and concentrated to give a gum. This was further purified by UV triggered HPLC, to give 3-chloro-5-cyanobenzyl 4-(2-(N-methyl-1H-1,2,3-triazole-4-carboxamido)ethyl)piperidine-1-carboxylate as a gum;

Workup

  1. customthe organic portion was separated
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in DCM
  5. washeluting with 0-100% EtOAc/iso-hexane
  6. concentrationconcentrated
  7. customto give a gum
  8. customThis was further purified by UV

Sources & evidence

ORD record
ord-90db1c2ae3004b14a29bb500e8919bcb
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409895B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes