Hydrochloric Acid → HCID 20789080, compound

HRID 1272913Notes

Reaction equation

HRID 1272913 reaction equation
O1C2C=CC=CC=2C=C1C1CCCOC1[N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]([NH:27][CH:28]([CH3:30])[CH3:29])=[O:26])=[CH:22][CH:23]=2)[CH:18]=[N:17]1.Cl.O1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>>[O:35]1[C:36]2[CH:37]=[CH:18][CH:19]=[CH:20][C:21]=2[CH:33]=[C:34]1[C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[C:21]([C:25]([NH:27][CH:28]([CH3:29])[CH3:30])=[O:26])[CH:20]=2)[NH:16][N:17]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131724915HCID 131724915, compound

Product 1

HCID 20789080HCID 20789080, compoundYield 7%

Procedure

(3-Benzo[d]furan-2-yl-1-perhydro-2H-pyran-2-yl(1H-indazol-5-yl))-N-(methylethyl)carboxamide (170 mg, 0.41 mmol) was taken up in a solution of 4 N HCl in dioxane and allowed to stir overnight. The reaction was neutralized to pH 7 and extracted with ethyl acetate. The organic layer was dried, filtered, and concentrated to yield the crude material which was purified by semi-preprative HPLC to yield the title compound (9 mg, 7% yield). 1H NMR (DMSO-d6) δ 13.8 (s, 1H), 8.7 (s, 1H), 8.4 (d, 1H), 8.0 (d, 1H), 7.6–7.8 (m, 4H), 7.4 (m, 2H), 4.2 (m, 1H), 3.2 (d, 1H), 1.2 (d, 6H).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield the crude material which
  6. customwas purified by semi-preprative HPLC

Sources & evidence

ORD record
ord-f51529f2cb4d440b9b7fccebe62a8581
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

Loading…