Hydrochloric Acid → HCID 20789119, compound

HRID 1353804Notes

Reaction equation

HRID 1353804 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]5[N:31]=[CH:30][N:29](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[N:28]=5)[CH:25]=4)[N:20](C4CCCCO4)[N:19]=3)[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[NH:28]1[C:27]([C:24]2[CH:25]=[C:26]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:14]2[CH:13]=[C:12]([C:10]([NH:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:11])[CH:17]=[CH:16][CH:15]=2)=[N:31][CH:30]=[N:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22479758HCID 22479758, compound

Product 1

HCID 20789119HCID 20789119, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of N-[(4-fluorophenyl)methyl](3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)carboxamide (0.423 g, 0.573 mmol) was added dioxane (4.0 mL) and aqueous 6 N hydrochloric acid (4.0 mL) and the mixture heated at 50° C. for 5.5 h. The mixture was cooled and poured into saturated sodium bicarbonate (50 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and evaporated. Addition of ethyl acetate (5 mL) initiated crystal growth and the ethyl acetate phase was pipetted off. The crystals were filtered. Purification by preparative HPLC (30–80% acetonitrile/water) followed by washing with saturated sodium bicarbonate and extraction with ethyl acetate gave the title compound (0.0723 g, 31% yield). 1H NMR (CD3OD) δ 8.78 (s, 1H), 8.49 (t, 1H), 8.22 (dt, 1H), 8.13 (d, 1H), 7.94 (dt, 1H), 7.70 (d, 1H), 7.68 (t, 1H), 7.43 (m, 2H), 7.07 (m, 2H), 4.60 (s, 2H). ES-MS (m/z) 413 [M+1]+

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with saturated sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. additionAddition of ethyl acetate (5 mL)
  8. filtrationThe crystals were filtered
  9. customPurification by preparative HPLC (30–80% acetonitrile/water)
  10. washby washing with saturated sodium bicarbonate and extraction with ethyl acetate

Sources & evidence

ORD record
ord-efee99f3f2124a719dd80c4839645e55
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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