Hydrochloric Acid → HCID 68502542, compound

HRID 1712981Notes

Reaction equation

HRID 1712981 reaction equation
[Si]([O:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([NH:15][C:16]([N:18]2[CH2:23][CH2:22][O:21][C:20]3[CH:24]=[C:25]([O:28][C:29]4[C:38]5[C:33](=[CH:34][C:35]([O:41][CH3:42])=[C:36]([O:39][CH3:40])[CH:37]=5)[N:32]=[CH:31][CH:30]=4)[CH:26]=[CH:27][C:19]2=3)=[O:17])[CH:11]=1)(C(C)(C)C)(C)C.[ClH:43]>CCO>[ClH:43].[CH3:40][O:39][C:36]1[CH:37]=[C:38]2[C:33](=[CH:34][C:35]=1[O:41][CH3:42])[N:32]=[CH:31][CH:30]=[C:29]2[O:28][C:25]1[CH:26]=[CH:27][C:19]2[N:18]([C:16]([NH:15][C:12]3[CH:11]=[C:10]([CH2:9][OH:8])[O:14][N:13]=3)=[O:17])[CH2:23][CH2:22][O:21][C:20]=2[CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57737146HCID 57737146, compound

Product 1

HCID 68502542HCID 68502542, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To N-(5-((tert-butyldimethylsilyloxy)methyl)isoxazol-3-yl)-7-(6,7-dimethoxyquinolin-4-yloxy)-2,3-dihydrobenzo[b][1,4]oxazine-4-carboxamide (7) (50 mg, 0.084 mmol) was added 2 N HCl in EtOH (5 mL) at RT. After 15 min, the solid had dissolved and the solution was stirred at RT for an additional 2 hrs at which time a white precipitate formed. The mixture was cooled to 0° C., filtered, and the isolated solid was washed with cold EtOH. The solid was dried in vacuo to afford 7-(6,7-dimethoxyquinolin-4-yloxy)-N-(5-(hydroxymethyl)isoxazol-3-yl)-2,3-dihydrobenzo[b][1,4]oxazine-4-carboxamide hydrochloride (33 mg, 83% yield). MH+=479.2.

Workup

  1. dissolutionthe solid had dissolved
  2. customformed
  3. temperatureThe mixture was cooled to 0° C.
  4. filtrationfiltered
  5. washthe isolated solid was washed with cold EtOH
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-799526408f744a91ba028dc7dcd9b233
Source dataset
uspto-grants-2010_09
Patent number
US07795254B2

Reaction notes

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