Water → HCID 11654827, compound

HRID 646848Notes

Reaction equation

HRID 646848 reaction equation
[N:1]1([C:7]2[CH:12]=[C:11]([N:13]3[CH2:18][CH2:17][S:16][CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:19][C:20]([C:22]2[O:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=2)=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[N+]1([O-])CC[O:33]CC1.[OH2:37]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[O:37]=[S:16]1(=[O:33])[CH2:15][CH2:14][N:13]([C:11]2[CH:10]=[CH:9][C:8]([NH:19][C:20]([C:22]3[O:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=3)=[O:21])=[C:7]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:12]=2)[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 11545711HCID 11545711, compound

Product 1

HCID 11654827HCID 11654827, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of 21.5 mg (0.0542 mmol) 5-cyano-furan-2-carboxylic acid (2-piperidin-1-yl-4-thiomorpholin-4-yl-phenyl)-amide (as prepared in Example 6, step (b)) in 0.6 mL of acetone-water (3:1) was added 22.0 mg (0.163 mmol) of 4-methyl-morpholine N-oxide followed by 25 μL (0.0039 mmol) of a solution of osmium tetroxide (4.0 wt % in water). After stirring for 18 h at RT, 3 mL of water was added and the mixture extracted with EtOAc (2×5 mL). The combined extracts were washed with brine (5 mL), dried (Na2SO4) and concentrated. Chromatography of the resulting residue on a 5-g silica SPE column with 5-6% EtOAc-dichloromethane afforded 19.1 mg (82%) of the title compound as a light yellow solid: 1H-NMR (CDCl3; 400 MHz): δ 9.48 (br s, 1H), 8.36 (d, 1H, J=8.9 Hz), ca. 7.28 (d, 1H, J=3.7 Hz), 7.23 (d, 1H, J=3.7 Hz), 6.77 (d, 1H, J=2.7 Hz), 6.73 (dd, 1H, J=8.9, 2.7 Hz), 3.80 (m, 4H), 3.14 (m, 4H), 2.84 (m, 4H), 1.82 (m, 4H), and 1.67 (br m, 2H). Mass spectrum (ESI, m/z): Calcd. for C21H24N4O4S, 429.2 (M+H), found 429.1.

Workup

  1. extractionthe mixture extracted with EtOAc (2×5 mL)
  2. washThe combined extracts were washed with brine (5 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-69490ee3600c44f2aff1de9805bdd88b
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

Loading…