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Hydrochloric Acid → HCID 178451481, compound

HRID 710468
Notes
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Reaction equation

HRID 710468 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]2)#[N:2].Cl.[NH2:20][OH:21].CCN(C(C)C)C(C)C>CCO>[OH:21][NH:20][C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]2)=[NH:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 81531DiisopropylethylamineHCID 18630967tert-Butyl 5-cyano-1,3-dihydro-2H-isoindole-2-carboxylate

Product 1

HCID 178451481HCID 178451481, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

A product of Step C (0.22 g; 0.904 mmol), HCl×NH2OH (0.16 g; 2.3 mmol) and DIPEA (0.48 ml; 5 mmol) in anhydrous EtOH (3.5 ml) was refluxed for 2 h under N2. The solvents were removed under reduced pressure and the residue was diluted to 30 ml with EtOAc, washed with H2O (2×5 ml), brine, dried over anhydrous MgSO4, filtered and the filtrate evaporated to dryness to give the title compound (0.25 g; 100%) as colourless foam, which was used in next step without further purification.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe residue was diluted to 30 ml with EtOAc
  3. washwashed with H2O (2×5 ml), brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-b59620437afd4f83861a8cb69e00ba44
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181182B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes