Trifluoroacetic acid → HCID 11488654, compound

HRID 1784468Notes

Reaction equation

HRID 1784468 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]2=[N:10][C:9]=1[CH:19]([N:23]([CH2:33][CH2:34][CH2:35][N:36]1C(=O)C2C(=CC=CC=2)C1=O)[C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)[CH:20]([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN.C(O)(C(F)(F)F)=O>C(O)C>[NH2:36][CH2:35][CH2:34][CH2:33][N:23]([CH:19]([C:9]1[N:10]=[C:11]2[CH2:18][CH2:17][CH2:16][CH2:15][N:12]2[C:13](=[O:14])[C:8]=1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:20]([CH3:21])[CH3:22])[C:24](=[O:32])[C:25]1[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 57593200HCID 57593200, compound

Product 1

HCID 11488654HCID 11488654, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Step 12 (22), 50 mg (0.08 mmol) was dissolved in 1 ml of anhydrous ethanol. Hydrazine 18 μl (0.57 mmol) was added and the reaction stirred at room temperature for 2 h. The precipitate was filtered through a PTFE filter and washed with ethyl acetate. The solvent was evaporated and the crude material was purified by reverse phase HPLC resulting to 11 mg (0.023 mmol) of N-(3-aminopropyl)-N-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]-4-methylbenzamide (2) as the TFA salt.

Workup

  1. filtrationThe precipitate was filtered through a PTFE
  2. filtrationfilter
  3. washwashed with ethyl acetate
  4. customThe solvent was evaporated
  5. customthe crude material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-569b44ae1a804b5881ce58036529f28d
Source dataset
uspto-grants-2009_03
Patent number
US07504405B2

Reaction notes

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