Formic Acid → HCID 22480197, compound

HRID 1353796Notes

Reaction equation

HRID 1353796 reaction equation
[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][N:10]=[C:9]3[C:15]2[CH:16]=[C:17]([CH:32]=[CH:33][CH:34]=2)[O:18][CH2:19][CH2:20][NH:21]C(OCC2C=CC=CC=2)=O)=[N:4][CH:3]=[N:2]1.C(O)=O>[Pd].CO>[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][N:10]=[C:9]3[C:15]2[CH:16]=[C:17]([CH:32]=[CH:33][CH:34]=2)[O:18][CH2:19][CH2:20][NH2:21])=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 22480193HCID 22480193, compound

Product 1

HCID 22480197HCID 22480197, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-{2-[3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenoxy]ethyl}(phenylmethoxy)carboxamide (0.056 g, 0.123 mmol) was treated with formic acid (2 mL), methanol (0.088 mL) and 10% palladium on carbon (0.060 g) under nitrogen for 3 h. The mixture was filtered though Celite and concentrated. The residue was taken up in aqueous 6 N hydrochloric acid and extracted with ether (3×). The aqueous layer was adjusted to pH 11 and extracted with dichloromethane. The organic fractions were dried over anhydrous sodium sulfate, filtered and evaporated. The residue was purified by preparative HPLC (30–80% acetonitrile/water) and gave the title compound (0.0062 g, 16% yield) as the mono trifluoroacetic acid salt. 1H NMR (CD3OD) δ 8.77 (d, 1H), 8.54 (s, 1H), 8.12 (dd, 1H), 7.73 (m, 1H), 7.70 (m, 1H), 7.65 (m, 1H), 7.54 (t, 1H), 7.13 (m, 1H), 4.38 (t, 2H), 3.44 (t, 2H). ES-MS (m/z) 321 [M+1]+

Workup

  1. filtrationThe mixture was filtered though Celite
  2. concentrationconcentrated
  3. extractionextracted with ether (3×)
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic fractions were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by preparative HPLC (30–80% acetonitrile/water)

Sources & evidence

ORD record
ord-d5cc4a7e206740f0a35289986290de7e
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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