Potassium cyanate → HCID 44467320, compound

HRID 2381628Notes

Reaction equation

HRID 2381628 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:14]([F:15])=[CH:13][N:12]=[C:11]([NH:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]4)[N:10]=2)[CH2:5][CH2:4]1.[O-:28][C:29]#[N:30].[K+]>CC#N.O>[F:15][C:14]1[C:9]([N:6]2[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:29]([NH2:30])=[O:28])[CH2:4][CH2:5]2)=[N:10][C:11]([NH:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]3)=[N:12][CH:13]=1

Participants

5

Reactant 2

HCID 11378442Potassium cyanateHCID 44467019HCID 44467019, compound

Product 1

HCID 44467320HCID 44467320, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 6-(4-(4-(aminomethyl)piperidin-1-yl)-5-fluoropyrimidin-2-ylamino)-3,4-dihydroquinolin-2(1H)-one (26 mg, 0.070 mmol) in CH3CN (1 mL), an aqueous solution of potassium cyanate (34 mg, 0.42 mmol) in H2O (1 mL) was added. The mixture was stirred at 70° C. for 1 h. Solvents were removed in vacuo. The residue was purified by HPLC to give the titled compound (8 mg). MS 414.3 (M+H); UV 205.8, 276.8 nm

Workup

  1. customSolvents were removed in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-175ac21d16d54a9aab8818246505bf46
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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