Water → HCID 86619233, compound

HRID 426234Notes

Reaction equation

HRID 426234 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:43]=[C:44]([CH3:46])[CH:45]=1)[C:6]([C:8]1[N:13]([CH2:14][C:15]2[CH:16]=[C:17]([N:22](CC3C=CC(OC)=CC=3)[C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH:18]=[C:19]([F:21])[CH:20]=2)[C:12](=[O:38])[NH:11][C:10](=[O:39])[C:9]=1[CH:40]([CH3:42])[CH3:41])=[O:7])#[N:2].O>C(#N)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:43]=[C:44]([CH3:46])[CH:45]=1)[C:6]([C:8]1[N:13]([CH2:14][C:15]2[CH:16]=[C:17]([NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH:18]=[C:19]([F:21])[CH:20]=2)[C:12](=[O:38])[NH:11][C:10](=[O:39])[C:9]=1[CH:40]([CH3:41])[CH3:42])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 962WaterHCID 59184802HCID 59184802, compound

Product 1

HCID 86619233HCID 86619233, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{3-[6-(3-Cyano-5-methyl-benzoyl)-5-isopropyl-2,4-dioxo-3,4-dihydro-2 H-pyrimidin-1-ylmethyl]-5-fluoro-phenyl}-2,2,2-trifluoro-N-(4-methoxy-benzyl)-acetamide (389 mg, 0.61 mmol) was dissolved in acetonitrile (6 ml). With stirring, ceric ammonium nitrate (669 mg, 1.2 mmol) and distilled water (3 ml) were added in this order. After 24 hr., the mixture was diluted with ethyl acetate, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexane (1:2)) to afford 240 mg (76%) of a white solid. 1H NMR (200 MHz, DMSO-d6) δ 1.03 (3H, d, J=6.8 Hz), 1.18 (3H, d, J=6.8 Hz), 2.09 (1H, m), 2.32 (3H, s), 4.42 (1H, d, J=16.8 Hz), 4.97 (1H, d, J=16.8 Hz), 6.80 (1H, m), 7.08 (1H, s), 7.31 (1H, m), 7.91 (1H, s), 7.96 (1H, s), 8.16 (1H, s), 11.28 (1H, s), 11.69 (1H, s).

Workup

  1. additionwere added in this order
  2. washwashed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent, EA:hexane (1:2))

Sources & evidence

ORD record
ord-84803832497c44c9866d253ffbaaaa54
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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