6-amino-3,4-dihydroquinolin-2(1H)-one → HCID 44467318, compound

HRID 2281547Notes

Reaction equation

HRID 2281547 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][NH:15]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)[C:5]([CH:23]2[CH2:25][CH2:24]2)=[CH:4][N:3]=1.[NH2:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32](=[O:37])[CH2:31][CH2:30]2>C(O)CCC.C(O)(C(F)(F)F)=O>[NH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][N:8]([C:6]2[C:5]([CH:23]3[CH2:24][CH2:25]3)=[CH:4][N:3]=[C:2]([NH:26][C:27]3[CH:28]=[C:29]4[C:34](=[CH:35][CH:36]=3)[NH:33][C:32](=[O:37])[CH2:31][CH2:30]4)[N:7]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 49127596-amino-3,4-dihydroquinolin-2(1H)-oneHCID 57990358HCID 57990358, compound

Product 1

HCID 44467318HCID 44467318, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
140 °C

Procedure

A solution of tert-butyl (1-(2-chloro-5-cyclopropylpyrimidin-4-yl)piperidin-4-yl)methylcarbamate (99 mg, 0.27 mmol) and 6-amino-3,4-dihydroquinolin-2(1H)-one (50 mg, 0.30 mmol) in nBuOH (3 mL) was stirred at 116° C. for 20 h. It was then stirred at 140° C. for another 20 h. It was concentrated in vacuo. The residue was purified by HPLC to give a powder, which was then dissolved in TFA (3 mL). After being stirred at room temperature for 20 h, TFA was removed in vacuo. The residue was purified by HPLC to give the titled compound (16 mg). MS 393.5 (M+H); UV 208.9, 264.5 nm

Workup

  1. concentrationIt was concentrated in vacuo
  2. customThe residue was purified by HPLC
  3. customto give a powder, which
  4. stirringAfter being stirred at room temperature for 20 h
  5. customTFA was removed in vacuo
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-d4b10f3f4236400fad1ae5cecc2faa4b
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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