Triethylamine → HCID 59551735, compound

HRID 1170232Notes

Reaction equation

HRID 1170232 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.CCN(CC)CC.C(OC([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[C:41]3[C:36](=[CH:37][C:38](F)=[CH:39][CH:40]=3)[N:35]=[CH:34][N:33]=2)[CH2:28][CH2:27]1)=O)(C)(C)C>CN(C=O)C.O>[CH3:11][N:8]1[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:38]2[CH:37]=[C:36]3[C:41]([C:32]([CH:29]4[CH2:30][CH2:31][NH:26][CH2:27][CH2:28]4)=[N:33][CH:34]=[N:35]3)=[CH:40][CH:39]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 595517364-(7-Fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59551735HCID 59551735, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-(3-aminopropyl)-1-methylpiperazine (0.1 mmol), Et3N (0.1 mmol) and 4-(7-fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.1 mmol), prepared as described in Example 12b, in DMF (1 mL) was stirred at 130° C. for 3 h. It was then diluted with water and extracted with EtOAc. The combined extracts were washed with water, brine, dried (anhydrous MgSO4), filtered and concentrated in vacuo. The crude product was then treated with 3M HCl/MeOH (2 mL) and stirred at rt for 2 h, then concentrated in vacuo.

Workup

  1. customprepared
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried (anhydrous MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe crude product was then treated with 3M HCl/MeOH (2 mL)
  8. stirringstirred at rt for 2 h
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad0ccbdb1fe64c74813210e19f2a2109
Source dataset
uspto-grants-2010_11
Patent number
US07825244B2

Reaction notes

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