Hydrochloric Acid → HCID 136041826, compound

HRID 880192Notes

Reaction equation

HRID 880192 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][O:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[NH:24][C:25](=[O:40])[CH2:26][C:27]2[NH:28][C:29](=[O:39])[CH:30]=[C:31]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:32]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>O1CCOCC1.C(O)C>[F:23][C:21]1[CH:20]=[CH:19][C:18]([NH:24][C:25](=[O:40])[CH2:26][C:27]2[NH:28][C:29](=[O:39])[CH:30]=[C:31]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)[N:32]=2)=[C:17]([O:16][CH2:15][CH:12]2[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]2)[CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136352210HCID 136352210, compound

Product 1

HCID 136041826HCID 136041826, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

1.5 ml of 4M hydrochloric acid in dioxane are added to a solution of 223 mg of 4-{5-fluoro-2-[2-(4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetylamino]phenoxymethyl}piperidine-1-carboxylic acid tert-butyl ester in 6 ml of ethanol. After stirring at ambient temperature for 20 h, the reaction medium is concentrated under reduced pressure, taken up with a solution of aqueous ammonia in methanol, and then again concentrated to dryness. After purification by silica column chromatography, eluent: 90/10 CH2Cl2/MeOH, 65 mg of N-[4-fluoro-2-(piperidin-4-ylmethoxy)phenyl]-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained, the characteristics of which are the following:

Workup

  1. concentrationthe reaction medium is concentrated under reduced pressure
  2. concentrationagain concentrated to dryness
  3. customAfter purification by silica column chromatography, eluent

Sources & evidence

ORD record
ord-293e94baa3314a4f85415eb947eda976
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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