Hydrochloric Acid → HCID 86607674, compound

HRID 412277Notes

Reaction equation

HRID 412277 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8]O)=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:23]2[C:28]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)=[CH:27][CH:26]=[CH:25][C:24]=2[O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[N:3]=1.[CH2:44]=[O:45].Cl>O1CCOCC1>[C:6]([CH:11]1[CH:10]([C:6]2[C:7]3[CH2:8][O:45][CH2:44][NH:1][C:2]=3[N:3]=[C:4]([C:23]3[C:28]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=4)=[CH:27][CH:26]=[CH:25][C:24]=3[O:39][CH2:40][CH:41]3[CH2:43][CH2:42]3)[CH:5]=2)[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])([CH3:10])([CH3:7])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 22258737HCID 22258737, compound

Product 1

HCID 86607674HCID 86607674, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 3-[2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-3-(hydroxymethyl)-4-pyridinyl]-1-piperidinecarboxylate (0.501 g, 0.850 mmol) in 1,4-dioxane was added 37% formaldehyde solution (5.000 mL) and 1N HCl (5.000 mL). The mixture was stirred at room temperature for 2 hrs. The reaction mixture was extracted with ethyl acetate and water. The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/hexane=3/2) to give 1,1-dimethylethyl (tert-butyl)-3-{7-[2-[(cyclopropylmethyl)oxy]-6-({[4-(methyloxy)phenyl]methyl}oxy)phenyl]-1,4-dihydro-2H-pyrido[2,3-d][1,3]oxazin-5-yl}-1-piperidinecarboxylate as a colorless foam (0.319 g, yield; 62%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate and water
  2. washThe separated organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel (ethyl acetate/hexane=3/2)

Sources & evidence

ORD record
ord-4b3be0b452234d2c94f88176ab663462
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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