HCID 11545711, compound → HCID 11704296, compound

HRID 646847Notes

Reaction equation

HRID 646847 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.I([O-])(=O)(=O)=[O:30].[Na+]>CO.CC#N.O>[O:30]=[S:16]1[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

5

Reactant 2

HCID 11545711HCID 11545711, compoundHCID 23667635Sodium periodate3×

Product 1

HCID 11704296HCID 11704296, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21959252Acetonitrile methanolSolvent

Procedure

To a solution of 25.3 mg (0.0638 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 2 mL of MeOH-MeCN (1:1) was added 15.0 mg (0.0702 mmol) of sodium periodate in 0.20 mL of water. After stirring for 1.5 h, an additional 4.1 mg (0.019 mmol) of sodium periodate was added. After stirring for 1.5 h, a final 9.5 mg (0.11 mmol) of sodium periodate was added and the mixture stirred for 24 h. The mixture was concentrated to near dryness, extracted with EtOAc (10 mL) and dried (Na2SO4). Concentration and chromatography on a 5-g silica SPE column with a gradient of 60-100% EtOAc-dichloromethane afforded 13.3 mg (51%) of the title compound as a light yellow solid: 1H-NMR (CDCl3; 400 MHz): δ 9.51 (br s, 1H), 8.35 (d, 1H, J=8.9 Hz), ca. 7.2 (d, 1H, obscured by CHCl3 peak), 7.23 (d, 1H, J=3.7 Hz), 6.81 (d, 1H, J=2.6 Hz), 6.77 (dd, 1H, J=8.9, 2.6 Hz), 3.94 (m, 2H), 3.51 (m, 2H), 2.91 (m, 4H), 2.85 (m, 4H), 1.81 (m, 4H), and 1.66 (br m, 2H). Mass spectrum (ESI, m/z): Calcd. for C21H24N4O3S, 413.2 (M+H), found 413.1.

Workup

  1. stirringAfter stirring for 1.5 h
  2. stirringthe mixture stirred for 24 h
  3. concentrationThe mixture was concentrated
  4. extractionextracted with EtOAc (10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration and chromatography on a 5-g silica SPE column with a gradient of 60-100% EtOAc-dichloromethane

Sources & evidence

ORD record
ord-c9b8631567d84146b7366ca14ca65c48
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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