HCID 71232774, compound → HCID 71232819, compound

HRID 869466Notes

Reaction equation

HRID 869466 reaction equation
COC1C=CC(C[N:8]2[C:17]([CH:18]([NH:20][C:21]3[C:22]4[N:30]=[CH:29][CH:28]=[CH:27][C:23]=4[N:24]=[CH:25][N:26]=3)[CH3:19])=[CH:16][C:15]3[N:14]=[CH:13][CH:12]=[C:11]([CH3:31])[C:10]=3[C:9]2=[O:32])=CC=1>FC(F)(F)C(O)=O>[CH3:31][C:11]1[C:10]2[C:9](=[O:32])[NH:8][C:17]([CH:18]([NH:20][C:21]3[C:22]4[N:30]=[CH:29][CH:28]=[CH:27][C:23]=4[N:24]=[CH:25][N:26]=3)[CH3:19])=[CH:16][C:15]=2[N:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 71232774HCID 71232774, compound

Product 1

HCID 71232819HCID 71232819, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
140 °C

Procedure

6-(4-Methoxybenzyl)-4-methyl-7-(1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl)-1,6-naphthyridin-5(6H)-one I-67 (60 mg, 0.13 mmol) was dissolved in trifluoroacetic acid (4 mL) in a sealed tube and the resulting mixture was stirred at 140° C. for 48 h. The mixture was allowed to cool to RT, quenched with water and then neutralized with saturated NaHCO3 aqueous solution. The mixture was extracted with ethyl acetate, washed with brine, dried with Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford the product, 4-methyl-7-(1-(pyrido[3,2-d]pyrimidin-4-ylamino)ethyl)-1,6-naphthyridin-5(6H)-one I-68. ESI-MS m/z: 333.2 [M+H]+.

Workup

  1. temperatureto cool to RT
  2. customquenched with water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-85eec952c7a942ebb48a2e75ed438c37
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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