Diisopropylethylamine → HCID 44467244, compound

HRID 2381766Notes

Reaction equation

HRID 2381766 reaction equation
C(OC([NH:11][CH:12]([CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O)C1C=CC=CC=1.Cl[C:26]1[N:31]=[C:30](Cl)[C:29]([F:33])=[CH:28][N:27]=1.CCN(C(C)C)C(C)C.[NH2:43][C:44]1[CH:45]=[C:46]2[C:51](=[CH:52][CH:53]=1)[NH:50][C:49](=[O:54])[CH2:48][CH2:47]2>CC#N>[NH2:11][CH:12]([CH:19]1[CH2:20][CH2:21][N:22]([C:28]2[C:29]([F:33])=[CH:30][N:31]=[C:26]([NH:43][C:44]3[CH:45]=[C:46]4[C:51](=[CH:52][CH:53]=3)[NH:50][C:49](=[O:54])[CH2:48][CH2:47]4)[N:27]=2)[CH2:23][CH2:24]1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 49127596-amino-3,4-dihydroquinolin-2(1H)-oneHCID 57990378HCID 57990378, compound

Product 1

HCID 44467244HCID 44467244, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 3-(benzyloxycarbonylamino)-3-(piperidin-4-yl)propanoate (102 mg, 0.305 mmol) and 2,4-dichloro-5-fluoropyrimidine (51 mg, 0.305 mmol) in CH3CN (2 mL), DIEA (0.106 mL, 0.610 mmol) was added. The mixture was stirred at room temperature for 68 h. It was then concentrated in vacuo. The residue was dissolved in nBuOH (3 mL), 6-amino-3,4-dihydroquinolin-2(1H)-one (82 mg, 0.506 mmol) was added. The solution was stirred at 116° C. for 20 h. It was concentrated in vacuo. The residue was dissolved in MeOH (9 mL). To the solution, Pd—C (10%, 40 mg) was added. The mixture was then hydrogenated under balloon hydrogen for 20 h. It was filtered through celite. The filtrate was concentrated in vacuo. The residue was purified by HPLC to give the titled compound (66 mg). MS 457.4 (M+H); UV 211.9, 277.3 nm.

Workup

  1. concentrationIt was then concentrated in vacuo
  2. dissolutionThe residue was dissolved in nBuOH (3 mL)
  3. stirringThe solution was stirred at 116° C. for 20 h
  4. concentrationIt was concentrated in vacuo
  5. dissolutionThe residue was dissolved in MeOH (9 mL)
  6. additionTo the solution, Pd—C (10%, 40 mg) was added
  7. waitThe mixture was then hydrogenated under balloon hydrogen for 20 h
  8. filtrationIt was filtered through celite
  9. concentrationThe filtrate was concentrated in vacuo
  10. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-0150133da8974d10b097e0670243165a
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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