Diethyl Ether → HCID 68832569, compound

HRID 1787928Notes

Reaction equation

HRID 1787928 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C([Mg]Cl)C=C.C(OCC)C.[C:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:30][C:31](=[O:39])[C:32]3[CH:38]=[N:37][CH:36]=[CH:35][C:33]=3[N:34]=2)=[C:25]([O:40][CH:41]2[CH2:46][CH2:45][N:44]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][CH2:42]2)[CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>C1COCC1.C(OCC)(=O)C>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([NH:34][C:33]2[CH:35]=[CH:36][N:37]=[CH:38][C:32]=2[C:31]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=2)=[O:39])=[O:30])=[C:25]([O:40][CH:41]2[CH2:42][CH2:43][N:44]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:45][CH2:46]2)[CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 661742-Amino-5-chloropyridineHCID 68832536HCID 68832536, compoundHCID 178418473HCID 178418473, compound

Product 1

HCID 68832569HCID 68832569, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 2-amino-5-chloropyridine (0.055 g, 0.42 mmol) in THF (5 mL) at 0° C., was added a 1.0 M solution of allylmagnesium chloride in diethyl ether (0.4 mL, 0.4 mmol). To this solution was then added a solution of 2-[4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)-phenyl]-4H-pyrido[4,3-d][1,3]oxazin-4-one (0.12 g, 0.25 mmol) in THF (3 mL). After several hours, the solution was diluted with ethyl acetate and washed twice with brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo to give a white solid which was washed with diethyl ether and dried in vacuo to give the title compound (0.11 g, 70%).

Workup

  1. waitAfter several hours
  2. washwashed twice with brine
  3. dry with materialThe organic phase was then dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a white solid which
  7. washwas washed with diethyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-537320c1c2dc45428e4e3c3c3aaf4570
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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