Hydrochloric Acid → HCID 20789129, compound

HRID 1349739Notes

Reaction equation

HRID 1349739 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]5[N:27]=[CH:26][N:25](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[N:24]=5)[CH:21]=4)[N:16](C4CCCCO4)[N:15]=3)[CH:9]=2)=[O:7])[CH2:3][CH2:2]1.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[NH:24]1[C:23]([C:20]2[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[C:14]3[C:10]2[CH:9]=[C:8]([C:6]([NH:5][CH2:4][CH:1]3[CH2:3][CH2:2]3)=[O:7])[CH:13]=[CH:12][CH:11]=2)=[N:27][CH:26]=[N:25]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22480338HCID 22480338, compound

Product 1

HCID 20789129HCID 20789129, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of N-(cyclopropylmethyl)(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl) (1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)carboxamide (0.241 g, 0.352 mmol) was added dioxane (4.0 mL) and aqueous 6 N hydrochloric acid (4.0 mL) and the mixture heated at 50° C. for 4 h. The mixture was cooled and poured into aqueous 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) gave the title compound (0.0682 g, 54% yield). 1H NMR (CD3OD) δ 8.79 (s, 1H), 8.45 (m, 1H), 8.19 (dt, 1H), 8.11 (d, 1H), 7.90 (dt, 1H), 7.69 (d, 1H), 7.66 (t, 1H), 3.30 (m, 2H), 1.18 (m, 1H), 0.55 (m, 2H), 0.32 (m, 2H). ES-MS (m/z) 359 [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)

Sources & evidence

ORD record
ord-2efb91156fff418cb79c51fff8eefeee
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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