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Sodium Iodide → HCID 23294184, compound

HRID 1377479
Notes
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Reaction equation

HRID 1377479 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

The title compound is prepared according to the procedure described for example 7 starting from 8-amino-3-formyl-2-methylimidazo[1,2-a]pyridine (4.0 g), 2-tert-butoxycarbonylamino-6-methylbenzylchloride (7.0 g), sodium iodide (4.1 g) and sodium carbonate (6.1 g) in acetone (250 ml). Purification by chromatography on silica gel (toluene/dioxane 9:1 as eluent) and crystallization from diisopropyl ether yield 7.3 g (81%) of m.p. 210°-212° C.

Workup

  1. customPurification by chromatography
  2. customon silica gel (toluene/dioxane 9:1 as eluent) and crystallization from diisopropyl ether yield 7.3 g (81%) of m.p. 210°-212° C.

Sources & evidence

ORD record
ord-3afafba3e027475987a3099139328cc9
Source dataset
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05665730

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes