Trifluoroacetic acid → HCID 59726982, compound

HRID 1363145Notes

Reaction equation

HRID 1363145 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:14]1[N:19]=[C:18]2[N:20]([C@@H:24]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH3:25])[C:21](=[O:23])[NH:22][C:17]2=[CH:16][CH:15]=1)C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[NH2:6][C:14]1[N:19]=[C:18]2[N:20]([C@@H:24]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH3:25])[C:21](=[O:23])[NH:22][C:17]2=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59727084HCID 59727084, compound

Product 1

HCID 59726982HCID 59726982, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-tert-butyl 2,4-dimethoxybenzyl(2-oxo-3-(1-(pyridin-3-yl)ethyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)carbamate in methylene chloride (15 mL) was treated with TFA (15 mL) and triethylsilane (1.0 mL) for one hour. The mixture was concentrated to provide the intermediate (R)-5-amino-3-(1-(pyridin-3-yl)ethyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (68), which was dissolved in acetonitrile (50 mL) and stirred vigorously with di-tert-butyl dicarbonate (1.0 g) and potassium carbonate (3.0 g) for 2 h. Methylene chloride (200 mL) and water (100 mL) was added and the organic layer was separated. The aqueous layer was extracted with another 100 mL of methylene chloride. The combined organic layers were separated, dried over sodium sulfate, filtered, and concentrated. Column chromatography (2→3→4% MeOH in methylene chloride) provided 235 mg (R)-tert-Butyl 5-amino-2-oxo-3-(1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (69).

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-0cad4e876e214d8db458858abb4b3113
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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