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

HRID 2281545Notes

Reaction equation

HRID 2281545 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-22565d9bb0a94509bddb6867c3b8a0a0
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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