(Diethylamino)sulfur trifluoride → 7-fluoro-1-((1R,4S)-4-fluorocyclopent-2-enyl)-1H-imidazo[4,5-c]pyridin-4-amine

HRID 470175Notes

Reaction equation

[NH2:1][C:2]1[C:7]2[N:8]=[CH:9][N:10]([C@@H:11]3[CH2:15][C@@H:14](O)[CH:13]=[CH:12]3)[C:6]=2[C:5]([F:17])=[CH:4][N:3]=1.CCN(S(F)(F)[F:24])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:17][C:5]1[C:6]2[N:10]([C@@H:11]3[CH2:15][C@H:14]([F:24])[CH:13]=[CH:12]3)[CH:9]=[N:8][C:7]=2[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(1R,4R)-4-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopent-2-enol (4-3) (600 mg, 2.6 mmol, 1 eq) was dissolved in DCM (120 mL). The mixture was cooled to 0° C. and DAST (1.6 mL, 12.0 mmol, 4.7 eq) was added. The resulting mixture was stirred at the same temperature for 1 hour. Upon disappearance of starting material, the reaction mixture was poured over NaHCO3 (30 mL) and extracted with CHCl3 (3×50 mL). The combined organics were dried over MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography (0-100% Acetone in DCM) to afford 7-fluoro-1-((1R,4S)-4-fluorocyclopent-2-enyl)-1H-imidazo[4,5-c]pyridin-4-amine (4-5) as a white solid. LRMS m/z (M+H) 236.9.0 found, 237.1 required.

Workup

extractionextracted with CHCl3 (3×50 mL)
dry with materialThe combined organics were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified by flash chromatography (0-100% Acetone in DCM)

Sources & evidence

ORD record: ord-2ca1964cfd8d4c58b4fb210623257556
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629275B2

Reaction notes

Loading…