Hydrochloric Acid → HCID 22479852, compound

HRID 1349760Notes

Reaction equation

HRID 1349760 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[N:20]=[CH:19][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:17]=3)=[CH:13][CH:14]=2)[C:9]([C:40]2[CH:41]=[C:42]([C:46]([N:48]3[CH2:56][C:55]4[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=4)C3)=O)[CH:43]=[CH:44][CH:45]=2)=[N:8]1.Cl.[C:58](=[O:61])(O)[O-].[Na+]>O1CCOCC1>[NH:17]1[C:16]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][N:8]=[C:9]3[C:40]2[CH:41]=[C:42]([CH:46]3[C:50]4[C:55](=[CH:54][CH:53]=[CH:52][CH:51]=4)[CH2:56][N:48]3[C:58]([N:48]3[CH2:56][C:55]4[C:54](=[CH:53][CH:52]=[CH:51][CH:50]=4)[CH:46]3[C:42]3[CH:43]=[CH:44][CH:45]=[C:40]([C:9]4[C:10]5[C:15](=[CH:14][CH:13]=[C:12]([C:16]6[NH:17][N:18]=[CH:19][N:20]=6)[CH:11]=5)[NH:7][N:8]=4)[CH:41]=3)=[O:61])[CH:43]=[CH:44][CH:45]=2)=[N:20][CH:19]=[N:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22480212HCID 22480212, compound

Product 1

HCID 22479852HCID 22479852, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of isoindolin-2-yl 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl ketone (0.240 g, 0.327 mmol) was added 4.0 M hydrochloric acid in dioxane (10.0 mL) and the mixture stirred at ambient temperature for 20 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 (0.0458 g, 34% yield). 1H NMR (CD3OD) δ 8.74 (s, 1H), 8.50 (br s, 1H), 8.23 (s, 1H), 8.19 (m, 1H), 8.10 (br s, 1H), 7.68 (m, 3H), 7.37 (d, 1H), 7.26 (m, 3H), 5.00 (s, 2H), 4.93 (s, 2H). ES-MS (m/z) 407 [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-2166deb0f9f94eadbc005168fa28f83e
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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