6-amino-3,4-dihydroquinolin-2(1H)-one → HCID 44467317, compound

HRID 2381771Notes

Reaction equation

HRID 2381771 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]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:4][N:3]=1.[NH2:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[NH:36][C:35](=[O:40])[CH2:34][CH2:33]2>C(O)CCC>[NH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][N:8]([C:6]2[C:5]([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)=[CH:4][N:3]=[C:2]([NH:29][C:30]3[CH:31]=[C:32]4[C:37](=[CH:38][CH:39]=3)[NH:36][C:35](=[O:40])[CH2:34][CH2:33]4)[N:7]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 49127596-amino-3,4-dihydroquinolin-2(1H)-oneHCID 57990339HCID 57990339, compound

Product 1

HCID 44467317HCID 44467317, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of tert-butyl (1-(2-chloro-5-(pyridin-4-yl)pyrimidin-4-yl)piperidin-4-yl)methylcarbamate (80 mg, 0.20 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 concentrated in vacuo. The residue was dissolved in TFA (4 mL). After being stirred at room temperature for 30 min, TFA was removed in vacuo. The residue was purified by HPLC to give the titled compound. MS 430.4 (M+H); UV 207.7, 264.5 nm.

Workup

  1. concentrationIt was concentrated in vacuo
  2. dissolutionThe residue was dissolved in TFA (4 mL)
  3. customTFA was removed in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-ce86744888414af9a1cb3edef2584716
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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