2H-[1,3]Dioxolo[4,5-b]pyridin-7-amine → HCID 68541724, compound

HRID 2374435Notes

Reaction equation

HRID 2374435 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[N:18][C:19](Cl)=[N:20]3)=[C:15]([O:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:14]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[NH2:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]2[O:38][CH2:39][O:40][C:33]=12>N.C(Cl)Cl>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17]([NH:31][C:32]4[CH:37]=[CH:36][N:35]=[C:34]5[O:38][CH2:39][O:40][C:33]=45)=[N:18][CH:19]=[N:20]3)=[C:15]([O:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:14]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 450794752H-[1,3]Dioxolo[4,5-b]pyridin-7-amineHCID 86605299HCID 86605299, compound

Product 1

HCID 68541724HCID 68541724, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent

Procedure

Using an analogous procedure to that described in Example 1, 7-[2-(4-acetylpiperazin-1-yl)ethoxy]chloro-5-tetrahydropyran-4-yloxyquinazoline (0.113 g) was reacted with 4-amino-2,3-methylenedioxypyridine (0.036 g). The reaction mixture was quenched with glacial acetic acid (0.031 g) and diluted with methanol. The mixture was evaporated and the residue was purified by column chromatography on a C18 reversed phase silica column (Waters Symmetry column, 5 microns silica, 20 mm diameter, 100 mm length) using a decreasingly polar mixture of water and acetonitrile (containing 1% acetic acid) as eluent. The material so obtained was diluted with a 7M methanolic ammonia solution. The mixture was evaporated and the material so obtained was dissolved in methylene chloride. The solution was dried over magnesium sulphate and evaporated to give the title compound as a foam in 53% yield; NMR Spectrum: (CDCl3) 2.02 (m, 2H), 2.1 (s, 3H), 2.22 (m, 2H), 2.6 (m, 4H), 2.9 (m, 2H), 3.51 (m, 2H), 3.6 (m, 2H), 3.66 (m, 2H), 4.1 (m, 2H), 4.25 (m, 2H), 4.73 (m, 1H), 6.13 (s, 2H), 6.59 (s, 1H), 6.9 (s, 1H), 7.7 (d, 1H), 8.36 (d, 1H), 8.66 (s, 1H); Mass Spectrum: M+H+ 537.

Workup

  1. customThe reaction mixture was quenched with glacial acetic acid (0.031 g)
  2. additiondiluted with methanol
  3. customThe mixture was evaporated
  4. customthe residue was purified by column chromatography on a C18 reversed phase silica column (Waters Symmetry column, 5 microns silica, 20 mm diameter, 100 mm length)
  5. additiona decreasingly polar mixture of water and acetonitrile (containing 1% acetic acid) as eluent
  6. customThe material so obtained
  7. customThe mixture was evaporated
  8. customthe material so obtained
  9. dry with materialThe solution was dried over magnesium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-30691622d31143728105806ac8ac5f66
Source dataset
uspto-grants-2008_12
Patent number
US07462623B2

Reaction notes

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