HCID 67189130, compound → HCID 59796444, compound

HRID 493088Notes

Reaction equation

HRID 493088 reaction equation
OC1C=C(C(O)CNC(C)(C)CCCC2C=C(OC)C3NC(=O)NC=3C=2)C2OCC(=O)NC=2C=1.Cl.C([O:43][C:44]1[CH:45]=[C:46]([CH:55]([OH:76])[CH2:56][NH:57][C:58]([CH3:75])([CH3:74])[CH2:59][CH2:60][CH2:61][N:62]2[C:66]3[CH:67]=[CH:68][CH:69]=[C:70]([O:71][CH3:72])[C:65]=3[NH:64][C:63]2=[O:73])[C:47]2[O:52][CH2:51][C:50](=[O:53])[NH:49][C:48]=2[CH:54]=1)C1C=CC=CC=1>CO.[Pd]>[OH:43][C:44]1[CH:45]=[C:46]([CH:55]([OH:76])[CH2:56][NH:57][C:58]([CH3:74])([CH3:75])[CH2:59][CH2:60][CH2:61][N:62]2[C:66]3[CH:67]=[CH:68][CH:69]=[C:70]([O:71][CH3:72])[C:65]=3[NH:64][C:63]2=[O:73])[C:47]2[O:52][CH2:51][C:50](=[O:53])[NH:49][C:48]=2[CH:54]=1

Participants

5

Reactant 2

HCID 67189130HCID 67189130, compoundHCID 68907046HCID 68907046, compound

Product 1

HCID 59796444HCID 59796444, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-hydroxy-8-{1-hydroxy-2-[4-(4-methoxy-2-oxo-2,3-dihydro-benzimidazol-6-yl)-1,1-dimethyl-butylamino]-ethyl}-4H-benzo[1,4]oxazin-3-one: 130 mg (0.213 mmol) 6-benzyloxy-8-{1-hydroxy-2-[4-(4-methoxy-2-oxo-2,3-dihydro-benzimidazol-1-yl)-1,1-dimethyl-butylamino]-ethyl}-4H-benzo[1,4]oxazin-3-one hydrochloride are dissolved in methanol and hydrogenated at normal pressure with palladium on charcoal as catalyst. The catalyst is filtered through Celite, the filtrate is freed from the solvent and the residue is stirred with ethyl acetate. Solid. Yield: 50 mg (45%, hydrochloride); mass spectroscopy: [M+H]+=471.

Workup

  1. filtrationThe catalyst is filtered through Celite

Sources & evidence

ORD record
ord-bcff430983164d2188f6caea3383a76b
Source dataset
uspto-grants-2009_05
Patent number
US07534789B2

Reaction notes

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