1,2-Dimethoxyethane → HCID 86633103, compound

HRID 1012207Notes

Reaction equation

HRID 1012207 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:4]=1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[C:14]2[S:18][C:17](=[S:19])[NH:16][C:15]2=[O:20])=[CH:9][C:8]=1[O:21][CH3:22].COCCOC.[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>CCOC(C)=O.C(O)(=O)C>[F:32][C:2]([F:1])([F:31])[C:3]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:4]=1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]2[S:18][C:17](=[S:19])[NH:16][C:15]2=[O:20])=[CH:9][C:8]=1[O:21][CH3:22]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 72994854HCID 72994854, compound

Product 1

HCID 86633103HCID 86633103, compoundYield 368%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a N2-purged flask was added ′5-[1-[4-(2,4-bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-methylidene]-2-thioxo-thiazolidin-4-one (42 mg, 85 μmol) and DME (4 mL). To the solution was added NaBH3CN (20 mg, 255 μmol) followed by acetic acid (2 mL). The reaction was stirred at rt for 2 h. The reaction solution was then diluted with EtOAc (100 mL), neutralized by successive washings of sat NaHCO3 (100 mL×3), washed with sat. NaCl (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was chromatographed (SiO2, DCM/MeOH 100:0 to 98:2) to provide intermediate compound (155 mg, 50% yield). 1H NMR (CDCl3) δ 9.29 (1H, br s), 7.99 (1H, d, J=8.1 Hz), 7.94 (1H, s), 7.83 (1H, d, J=8.1 Hz), 6.72-6.81 (3H, m), 5.38 (2H, s), 4.60 (1H, dd, J1=3.9 Hz, J2=9.8 Hz), 3.92 (3H, s), 3.48 (1H, dd, J=3.9 Hz, J2=14.2 Hz), 3.14 (1H, m); MS (ESI) 496 (MH+).

Workup

  1. customTo a N2-purged flask
  2. washwashed with sat. NaCl (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was chromatographed (SiO2, DCM/MeOH 100:0 to 98:2)

Sources & evidence

ORD record
ord-4996c4ff91a74336a8a7700efd8f84dd
Source dataset
uspto-grants-2011_07
Patent number
US07977489B2

Reaction notes

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