Triethylamine → HCID 135939103, compound

HRID 591628Notes

Reaction equation

HRID 591628 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:27])[NH:6][C:7]([C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=1)=[N:8]2.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[F:57][C:58]([F:64])([F:63])[CH2:59][C:60](O)=[O:61]>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:27])[NH:6][C:7]([C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH2:22][CH2:23][N:24]([C:60](=[O:61])[CH2:59][C:58]([F:64])([F:63])[F:57])[CH2:25][CH2:26]3)=[CH:17][CH:16]=1)=[N:8]2

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27779723,3,3-Trifluoropropionic acidHCID 1359390885,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinazolin-4(3H)-one

Product 1

HCID 135939103HCID 135939103, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinazolin-4(3H)-one (0.200 g, 0.54 mmol) in THF (10 mL) was added EDCl (0.105 g, 0.54 mmol), HOBt (0.074 g, 0.54 mmol), Et3N (0.08 mL, 0.54 mmol) and trifluoropropionic acid (0.070 g, 0.54 mmol). The reaction was stirred at room temperature for 4 hours and concentrated in vacuo. Purification by flash chromatography, eluting with 20% to 100% of 92:7:1 CHCl3/MeOH/concentrate NH4OH in CH2Cl2, afforded the title compound (0.135 g, 52%). 1H NMR (300 MHz, DMSO-d6): δ 11.78 (s, 1H), 8.10 (d, J=9.0 Hz, 2H), 7.03 (d, J=9.0 Hz, 2H), 6.68 (d, J=2.3 Hz, 1H), 6.47 (d, J=2.3 Hz, 1H), 3.88 (s, 3H), 3.83 (s, 3H), 3.70-3.78 (m, 2H), 3.60-3.67 (m, 4H), 3.34-3.38 (m, 4H). APCI MS m/z 477 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by flash chromatography
  3. washeluting with 20% to 100% of 92:7:1 CHCl3/MeOH/
  4. concentrationconcentrate NH4OH in CH2Cl2

Sources & evidence

ORD record
ord-906d6d65d5044ab6bb1f152284294f28
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

Loading…