TBAF tetrahydrofuran → HCID 66924218, compound

HRID 1360198Notes

Reaction equation

HRID 1360198 reaction equation
[NH:1]1[C:5]2=[C:6]3[CH:12]=[CH:11][NH:10][C:7]3=[N:8][CH:9]=[C:4]2[NH:3][C:2]1=[O:13].[F-].[CH2:15]([N+](CCCC)(CCCC)CCCC)[CH2:16][CH2:17][CH3:18].[O:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>O1CCCC1>[OH:32][CH2:36][CH:35]1[CH:17]2[CH2:18][CH:33]([CH2:15][CH2:16]2)[CH:34]1[N:1]1[C:5]2=[C:6]3[CH:12]=[CH:11][NH:10][C:7]3=[N:8][CH:9]=[C:4]2[NH:3][C:2]1=[O:13]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 58381976HCID 58381976, compound

Product 1

HCID 66924218HCID 66924218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{[(triisopropylsilyl)oxy]methyl}bicyclo[2.2.1]hept-2-yl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-2(1H)-one (45 mg) in tetrahydrofuran (0.15 ml) was added 1M tetrabutylammoniumfluoride/tetrahydrofuran solution (297 μl), and the mixture was stirred overnight at ambient temperature. The reaction solution was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol) to obtain 1-[3-(hydroxymethyl)bicyclo[2.2.1]hept-2-yl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-2(1H)-one (14.8 mg) as a white solid. To a solution of rel-4-{[(1R,2R,3S,5s)-5-hydroxyadamantan-2-yl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carbohydrazide in 1-methyl-2-pyrrolidone (1 ml) were added triethyl orthoformate (340 μl) and p-toluene sulfonic acid monohydrate (5.6 mg). After stirring at 120° C. for 30 minutes, triethyl orthoformate (340 μl) and p-toluene sulfonic acid monohydrate (5.6 mg) were added. After the mixture was stirred at 120° C. for 40 minutes, the reaction solution was extracted with 20% chloroform/methanol solution, and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol) to obtain rel-(1s,3R,4R,5S)-4-{[1-(diethoxymethyl)-5-(1,3,4-oxazole-2-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]amino}adamantan-1-ol (28 mg) and rel-(1s,3R,4R,5S)-4-{[5-(1,3,4-oxazole-2-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]amino}.adamantan-1-ol (70 mg).

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol)

Sources & evidence

ORD record
ord-91fe1735623048569bc90d95c752b805
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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