Sodium Chloride → HCID 21984334, compound

HRID 9432Notes

Reaction equation

HRID 9432 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:27][CH2:28][CH3:29])[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)=[CH:5][C:4]=2[N:3]=1.[OH-].[Na+].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>Cl.C(Cl)(Cl)Cl>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][C:6]([C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[C:13]1[CH2:27][CH2:28][CH3:29]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23549088HCID 23549088, compound

Product 1

HCID 21984334HCID 21984334, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of tert-butyl {4-[4-amino-2-propyl-7-(pyridin-3-yl)-1H-imidazol[4,5-c]quinolin-1-yl]butyl}carbamate (41.92 g, 88.32 mmol) in concentrated hydrochloric acid (210 mL) was stirred for ten minutes, and 50% aqueous sodium hydroxide was added to adjust the solution to pH 14. Cloroform (2.0 L) and a mixture of saturated aqueous sodium bicarbonate and 1% aqueous sodium carbonate (300 mL) were added. The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure to provide a yellow solid. The aqueous phase was treated with sodium chloride and chloroform (400 mL), and the mixture was stirred overnight. The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure to provide a yellow solid. The two solids were combined to yield 28.77 g of 1-(4-aminobutyl)-2-propyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine as a light yellow solid.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto provide a yellow solid
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto provide a yellow solid

Sources & evidence

ORD record
ord-8286c1f00f7142c681fea48b02e013db
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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