Sodium triacetoxyborohydride → HCID 68430759, compound

HRID 2090244Notes

Reaction equation

HRID 2090244 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=1)=O.[NH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[C:22]([NH2:31])[C:21]=2[N:20]=[C:19]1[CH2:32][O:33][CH2:34][CH3:35].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[NH2:31][C:22]1[C:21]2[N:20]=[C:19]([CH2:32][O:33][CH2:34][CH3:35])[N:18]([CH2:17][CH2:16][CH2:15][NH:14][CH2:1][C:3]3[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=3)[C:30]=2[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N:23]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11819590Methyl 2-(3-formylphenyl)acetateHCID 223444341-(3-Aminopropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 68430759HCID 68430759, compoundYield 4.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(3-formylphenyl)acetate (199 mg) was added to the product of step (iv) (334 mg) in THF (20 mL) at 25° C. under nitrogen. The resulting solution was stirred at rt for 6 h. Sodium triacetoxyborohydride (1183 mg) was added to the reaction mixture at rt under nitrogen and the mixture was stirred at rt for 15 h. The reaction mixture was quenched with water and dissolved in MeOH. The product was purified via RPHPLC, which afforded 25 mg of the desired product as a white solid.

Workup

  1. stirringthe mixture was stirred at rt for 15 h
  2. customThe reaction mixture was quenched with water
  3. dissolutiondissolved in MeOH
  4. customThe product was purified via RPHPLC, which

Sources & evidence

ORD record
ord-fb66db14b3e14294a64d61579d88dee1
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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