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Sodium Iodide → HCID 23294184, compound

HRID 1955009
Notes
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Reaction equation

HRID 1955009 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:14]([O:18][C:19]([NH:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH2:24]Cl)=[O:20])([CH3:17])([CH3:16])[CH3:15].[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[C:14]([O:18][C:19]([NH:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH2:24][NH:1][C:2]1[C:3]2[N:4]([C:8]([CH:12]=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 143684822-Tert-butoxycarbonylamino-6-methylbenzylchlorideHCID 21873989HCID 21873989, compound

Product 1

HCID 23294184HCID 23294184, compound

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

Starting from 8-amino-3-formyl-2-methylimidazo[1,2-a]pyridine (4.0 g), 2-tert-butoxycarbonylamino-6-methylbenzyl chloride (7.0 g), sodium iodide (4.1 g) and sodium carbonate (6.1 g) in acetone (250 ml) analogously using the process of Example B1 gives, after chromatography on silica gel (eluent toluene/dioxane 9:1) and recrystallization from diisopropyl ether, 7.3 g (81%) of the title compound of m.p. 210-212° C.

Workup

  1. customgives
  2. customafter chromatography on silica gel (eluent toluene/dioxane 9:1) and recrystallization from diisopropyl ether, 7.3 g (81%) of the title compound of m.p. 210-212° C.

Sources & evidence

ORD record
ord-d10e2bb10f4b4c63bc17c1b3691dd19a
Source dataset
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06124313

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes