Dichloromethane → HCID 178461107, compound

HRID 1852832Notes

Reaction equation

HRID 1852832 reaction equation
ClC1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:27][C@H:28]4[CH2:33][CH2:32][C@H:31]([CH3:34])[CH2:30][CH2:29]4)[C:15]([C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[F:26])(O)[CH3:18])=[N:16][C:12]=3[CH:11]=[C:10]([C:35]3[NH:39][C:38](=[O:40])[O:37][N:36]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1.C(N(S(F)(F)[F:47])CC)C.Cl[CH2:51][Cl:52]>>[Cl:52][C:51]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:27][C@H:28]4[CH2:33][CH2:32][C@H:31]([CH3:34])[CH2:30][CH2:29]4)[C:15]([C:17]([F:47])([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[F:26])[CH3:18])=[N:16][C:12]=3[CH:11]=[C:10]([C:35]3[NH:39][C:38](=[O:40])[O:37][N:36]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 123472(Diethylamino)sulfur trifluorideHCID 178466191HCID 178466191, compound

Product 1

HCID 178461107HCID 178461107, compound

Procedure

To a room temperature slurry of 3-{4-(5-chloropyridin-3-yl)-2-[1-(2-fluorophenyl)-1-hydroxyethyl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (38 mg, 0.067 mmol) in dichloromethane (1.35 mL) was added N,N-diethylaminosulfur trifluoride (0.045 mL, 0.337 mmol). The mixture was stirred for one hour, then quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane (2×). The combined organic layers were washed with brine (1×), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography (0-100% ethyl acetate/hexanes) to afford 3-{4-(5-chloropyridin-3-yl)-2-[1-fluoro-1-(2-fluorophenyl)ethyl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one as a white solid. MS ESI calcd. for C29H27ClF2N6O2 [M+H]+ 565. found 565. 1H NMR (500 MHz, DMSO-d6) δ 12.97 (s, 1H), 8.86 (s, 1H), 8.82 (s, 1H), 8.45 (s, 1H), 8.38 (s, 1H), 7.68-7.57 (m, 1H), 7.52-7.50 (m, 1H), 7.35-7.32 (m, 1H), 7.26-7.22 (m, 1H), 3.84-3.78 (m, 1H), 2.28 (d, J=23 Hz, 3H), 1.35-1.33 (m, 1H), 1.28-1.18 (m, 2H), 0.93-0.80 (m, 2H), 0.72-0.62 (m, 5H), 0.54-0.43 (m, 2H), 0.33-0.23 (m, 2H).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with dichloromethane (2×)
  3. washThe combined organic layers were washed with brine (1×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified via silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-94d130ca40024f699da2aff65138444a
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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