Hydrochloric Acid → HCID 178516495, compound

HRID 2183274Notes

Reaction equation

HRID 2183274 reaction equation
Cl.C(O[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[NH:6])C.[NH2:23][NH:24][C:25](=O)[CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]1.C[O-].[Na+].Cl>CO>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:5]4[NH:6][C:25]([CH2:26][N:27]5[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]5)=[N:24][N:23]=4)[CH:8]=3)[NH:12][N:11]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 22479739ethoxy[3-(4fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochlorideHCID 224803242-(4-Hydroxypiperidin-1-yl)acetohydrazide

Product 1

HCID 178516495HCID 178516495, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethoxy[3-(4-fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochloride (521 mg, 1.63 mmol), N-amino-2-(4-hydroxypiperidyl)acetamide (850 mg, 4.9 mmol), and sodium methoxide (1.2 mL, 4.9 mmol) in methanol (˜8 mL) was taken up in a sealed tube and allowed to stir at room temperature for 25 minutes and then heated at 95° C. overnight. The reaction was acidified with hydrochloric acid to neutral pH. The product was extracted using ethyl acetate. The material was concentrated and purified by semipreprative HPLC. The purified material was taken up in ethyl acetate and washed with an aqueous solution of sodium bicarbonate to yield the title compound (47 mg, 7% yield). 1H NMR (DMSO-d6) δ 13.4 (br s, 1H), 8.6 (s, 1H), 8.0 (m, 3H), 7.6 (m, 1H), 7.4 (t, 2H), 3.6-3.8 (m, 2H), 3.4 (m, 2H), 3.2 (d, 1H), 2.4 (m, 2H), 2.0 (s, 4H)H, ES-MS (m/z) 393 [M+1]+.

Workup

  1. temperatureheated at 95° C. overnight
  2. extractionThe product was extracted
  3. concentrationThe material was concentrated
  4. custompurified by semipreprative HPLC
  5. washwashed with an aqueous solution of sodium bicarbonate

Sources & evidence

ORD record
ord-2375395bff2a46cfa5301787417fdb62
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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