Water → HCID 178448640, compound

HRID 1931127Notes

Reaction equation

HRID 1931127 reaction equation
[CH2:1]([N:5]1[N:6]([CH3:28])[C:7]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:8]/[C:9]/1=[N:10]\[C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1F)[CH2:2][CH2:3][CH3:4].[SH:29][CH2:30][C:31]([NH2:33])=[O:32].C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[NH2:33][C:31](=[O:32])[CH2:30][S:29][C:13]1[CH:14]=[CH:15][C:16]([C:18]([F:21])([F:19])[F:20])=[CH:17][C:12]=1[C:11](/[N:10]=[C:9]1/[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:6]([CH3:28])[C:7]([C:24]([CH3:25])([CH3:27])[CH3:26])=[CH:8]/1)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 129612-MercaptoacetamideHCID 178448620HCID 178448620, compound

Product 1

HCID 178448640HCID 178448640, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of Example 81C (400 mg, 1 mmol), 2-mercaptoacetamide (183 mg, 2 mmol) and potassium carbonate (277 mg, 2 mmol) in DMA (10 mL) was heated at 50° C. for 14 hours. The mixture was then poured into water and extracted with ethyl acetate. The acetate layer was washed with brine, dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by chromatography (SiO2, EtOAc-MeOH: 9:1) afforded 235 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.81-1.02 (m, 3H), 1.27-1.44 (m, 11H), 1.56-1.78 (m, 2H), 3.55 (s, 2H), 3.88 (s, 3H), 4.27-4.50 (m, 2H), 6.83 (s, 1H), 7.12 (s, 1H), 7.41-7.73 (m, 3H), 8.32 (d, J=2.0 Hz, 1H). MS (ESI+) m/z 471 (M+H)+. Anal. calculated for C22H29F3N4O2S.0.25H2O: C, 55.62 H, 6.26 N, 11.79. Found: C, 55.46 H, 6.32 N, 11.50.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe acetate layer was washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by chromatography (SiO2, EtOAc-MeOH: 9:1)

Sources & evidence

ORD record
ord-56b644da34cb478ba67e58ee90327711
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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