Methanol → HCID 53241675, compound

HRID 1914910Notes

Reaction equation

HRID 1914910 reaction equation
C[N+]1([O-])CC[O:5][CH2:4]C1.[F:9][C:10]1C2C=COC=2[C:13]([NH:19][S:20]([C:23]2([CH2:26][CH:27]=C)[CH2:25][CH2:24]2)(=[O:22])=[O:21])=[C:12]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([I:36])=[CH:32][C:31]=2[F:37])[C:11]=1[F:38].C[OH:40].[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1>O.C(Cl)(Cl)Cl.[Os](=O)(=O)(=O)=O>[F:9][C:10]1[C:41]2[CH:42]=[CH:43][O:44][C:45]=2[C:13]([NH:19][S:20]([C:23]2([CH2:26][CH:27]([OH:40])[CH2:4][OH:5])[CH2:25][CH2:24]2)(=[O:22])=[O:21])=[C:12]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([I:36])=[CH:32][C:31]=2[F:37])[C:11]=1[F:38]

Participants

8

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 67235382HCID 67235382, compound

Product 1

HCID 53241675HCID 53241675, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
35 °C

Procedure

N-methyl morpholine oxide (0.035 g, 0.3041 mmol) was added to a solution of 1-allyl-cyclopropane sulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzofuran-7-yl]-amide (0.167 g, 0.3041 mmol) in THF (5 mL). This was followed by the addition of osmium tetroxide (0.0077 g, 0.03041 mmol) in water (1 mL). The reaction mass was stirred for 16 hours at 30-40° C. The reaction was monitored by TLC (10% methanol in chloroform). The reaction mass was partitioned between ethyl acetate (50 mL) and water. The organic layer was washed with water (3×50 mL), brine solution and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (5% methanol in chloroform) afforded 0.090 g of the product (50% yield). 1H NMR (CDCl3, 300 MHz): δ 7.69 (d, 2H), 7.40 (dd, 1H), 7.25 (s, 1H), 6.99 (d, 1H), 6.98 (bs, 1H), 6.38-6.40 (m, 1H), 4.25 (bs, 1H), 3.62 (dd, 2H), 3.32 (d, 1H), 2.55 (q, 1H), 2.22 (bs, 1H), 1.75 (t, 2H), 138-1.40 (m, 2H). LCMS: 99.49%, m/z=582.9 (M+1). HPLC: 95.29%

Workup

  1. customThe reaction mass was partitioned between ethyl acetate (50 mL) and water
  2. washThe organic layer was washed with water (3×50 mL), brine solution
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. customPurification by column chromatography on silica gel (5% methanol in chloroform)

Sources & evidence

ORD record
ord-cfce21484217482496d5224e34971d84
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

Loading…