Piperidine → HCID 22140789, compound

HRID 1826313Notes

Reaction equation

HRID 1826313 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:16][C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]4[O:24][CH2:25][O:26][C:18]=34)=[N:11][CH:12]=[N:13]2)=[C:8]([O:27][CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:7]=1.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:23][C:22]1[C:17]([NH:16][C:10]2[C:9]3[C:14](=[CH:15][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)=[CH:7][C:8]=3[O:27][CH:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[N:13]=[CH:12][N:11]=2)=[C:18]2[O:26][CH2:25][O:24][C:19]2=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 22140731HCID 22140731, compound

Product 1

HCID 22140789HCID 22140789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(3-bromopropoxy)-4-(6-chloro-2,3-methylenedioxyanilino)-5-tetrahydropyran-4-yloxyquinazoline (0.536 g), piperidine (0.12 ml), potassium carbonate (0.4 g) and DMF (2 ml) was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was triturated under methylene chloride. The mixture was filtered and the filtrate was purified by column chromatography on silica using initially a 1:1 mixture of ethyl acetate and methylene chloride and then a 10:9:1 mixture of ethyl acetate, methylene chloride and a saturated methanolic ammonia solution as eluent. There was thus obtained the title compound (0.53 g); NMR Spectrum: (CDCl3) 1.4–1.5 (m, 2H), 1.55–1.7 (m, 4H), 1.9–2.1 (m, 4H), 2.2–2.3 (m, 2H), 2.4 (m, 4H), 2.5 (m, 2H), 3.6–3.7 (m, 2H), 4.0–4.1 (m, 2H), 4.15 (m, 2H), 4.8 (m, 1H), 6.08 (s, 2H), 6.52 (d, 1H), 6.75 (d, 1H), 6.85 (d, 1H), 7.0 (d, 1H), 8.55 (s, 1H), 9.35 (s, 1H); Mass Spectrum: M+H+ 541 and 543.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated under methylene chloride
  3. filtrationThe mixture was filtered
  4. customthe filtrate was purified by column chromatography on silica using initially
  5. additiona 1:1 mixture of ethyl acetate and methylene chloride
  6. additiona 10:9:1 mixture of ethyl acetate, methylene chloride

Sources & evidence

ORD record
ord-01a228f87f8c419cab2e8f53effd2b80
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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