Hydrochloric Acid → HCID 68665434, compound

HRID 1893493Notes

Reaction equation

HRID 1893493 reaction equation
[F:1][C:2]([F:53])([F:52])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]1[C:13]([C:16]3[N:17](COCC[Si](C)(C)C)[N:18]=[CH:19][CH:20]=3)=[CH:14][N:15]=[C:8]1[C:7]([NH:29][CH2:30][CH2:31][CH2:32][O:33][P:34](=[O:51])([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[N:6]2.Cl.[Na]>C(O)C.C(O)(C)C>[N:18]1[NH:17][C:16]([C:13]2[N:9]3[C:10]4[C:5]([N:6]=[C:7]([NH:29][CH2:30][CH2:31][CH2:32][O:33][P:34](=[O:51])([O:43][CH2:44][C:45]5[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=5)[O:35][CH2:36][C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[C:8]3=[N:15][CH:14]=2)=[CH:4][C:3]([C:2]([F:1])([F:53])[F:52])=[CH:12][CH:11]=4)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 68664989HCID 68664989, compound

Product 1

HCID 68665434HCID 68665434, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of phosphoric acid dibenzyl ester 3-{7-trifluoromethyl-1-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]-imidazo[1,2-a]quinoxalin-4-ylamino}-propyl ester (966 mg; 1.26 mmol; 1.0 eq) in absolute ethanol (7 mL) at 0° C., is added a 4N solution of hydrogen chloride in isopropanol (3.5 mL). The solution is stirred for 5 minutes at 0° C., warmed-up to room temperature and stirred for two additional hours. The reaction mixture is basified with an aqueous solution saturated with sodium hydrogenocarbonate (35 mL). The aqueous layer is extracted three times with ethyl acetate (3×40 mL). The combined organic phases are dried over sodium sulphate, filtered and concentrated under vacuum. Purification by two successive silica gel chromatography (elution with ethyl acetate) afforded the title compound (392 mg; 0.61 mmol; 48%) as a colourless oil.

Workup

  1. temperaturewarmed-up to room temperature
  2. stirringstirred for two additional hours
  3. extractionThe aqueous layer is extracted three times with ethyl acetate (3×40 mL)
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification
  8. washby two successive silica gel chromatography (elution with ethyl acetate)

Sources & evidence

ORD record
ord-e691d92b202641d0be39e0133a81c714
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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