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Ammonium Chloride → HCID 118308740, compound

HRID 923507
Notes
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Reaction equation

HRID 923507 reaction equation
[C:1]([C:3]1([NH:11][C:12]([C:14]2[N:18]3[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH2:24][C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[C:17]3=[N:16][C:15]=2[CH3:33])=[O:13])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1)#[N:2].[Cl-].[NH4+].[N-:36]=[N+:37]=[N-:38].[Na+]>CN(C=O)C>[F:31][C:30]1[CH:29]=[CH:28][CH:27]=[C:26]([F:32])[C:25]=1[CH2:24][O:23][C:22]1[C:17]2[N:18]([C:14]([C:12]([NH:11][C:3]3([C:1]4[N:36]=[N:37][NH:38][N:2]=4)[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]3)=[O:13])=[C:15]([CH3:33])[N:16]=2)[CH:19]=[CH:20][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 118308702HCID 118308702, compound

Product 1

HCID 118308740HCID 118308740, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Under a nitrogen gas flow, to a solution of 27.7 g of N-(5-cyano-2,2-dimethyl-1,3-dioxan-5-yl)-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide in 280 ml of DMF were added 10.0 g of ammonium chloride and 12.0 g of sodium azide at room temperature, followed by stirring at 120° C. for 2 hours. The reaction mixture was left to be cooled to room temperature, and the insoluble materials were then separated by filtration and washed with DMF. The filtrate was added to water, followed by stirring at room temperature for 2 days. The resulting insoluble materials were separated by filtration and washed with water. The obtained residue was dried under reduced pressure to obtain 29.2 g of 8-[(2,6-difluorobenzyl)oxy]-N-[2,2-dimethyl-5-(2H-tetrazol-5-yl)-1,3-dioxan-5-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled to room temperature
  3. customthe insoluble materials were then separated by filtration
  4. washwashed with DMF
  5. additionThe filtrate was added to water
  6. stirringby stirring at room temperature for 2 days
  7. customThe resulting insoluble materials were separated by filtration
  8. washwashed with water
  9. customThe obtained residue was dried under reduced pressure

Sources & evidence

ORD record
ord-0811917e022849d39633f21851122eda
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278968B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes