Diisopropylethylamine → HCID 44467388, compound

HRID 2281404Notes

Reaction equation

HRID 2281404 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1.CCN(C(C)C)C(C)C.[NH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])[CH2:32][CH2:31]2>CC#N.C(O)CCC>[F:9][C:5]1[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]2)=[N:7][C:2]([NH:27][C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[NH:34][C:33](=[O:38])[CH2:32][CH2:31]3)=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 4207714-PiperidinemethanolHCID 49127596-amino-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 44467388HCID 44467388, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4-dichloro-5-fluoropyrimidine (167 mg, 1.00 mmol), 4-piperidinemethanol (115 mg, 1.00 mmol) and DIEA (0.400 mL, 2.30 mmol) in CH3CN (4 mL) was stirred at room temperature for 2 h. It was concentrated in vacuo. The residue was dissolved in nBuOH (6 mL). 3 mL of the nBuOH solution was taken, to which 6-amino-3,4-dihydroquinolin-2(1H)-one (88 mg, 0.54 mmol) was added. The solution was stirred at 116° C. for 20 h. nBuOH was removed in vacuo. The residue was purified by HPLC to give the titled compound (52 mg). MS 372.3 (M+H); UV 208.8, 275.8 nm.

Workup

  1. concentrationIt was concentrated in vacuo
  2. dissolutionThe residue was dissolved in nBuOH (6 mL)
  3. additionwas added
  4. customwas removed in vacuo
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-1a5656a6b1d840f78d3de6289b814f31
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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