Isonicotinic Acid → HCID 135939100, compound

HRID 591625Notes

Reaction equation

HRID 591625 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(CC)CC.[CH3:39][O:40][C:41]1[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[C:47]2[C:42]=1[C:43](=[O:65])[NH:44][C:45]([C:53]1[CH:58]=[CH:57][C:56]([N:59]3[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]3)=[CH:55][CH:54]=1)=[N:46]2>C1COCC1>[C:1]([N:62]1[CH2:63][CH2:64][N:59]([C:56]2[CH:57]=[CH:58][C:53]([C:45]3[NH:44][C:43](=[O:65])[C:42]4[C:47](=[CH:48][C:49]([O:51][CH3:52])=[CH:50][C:41]=4[O:40][CH3:39])[N:46]=3)=[CH:54][CH:55]=2)[CH2:60][CH2:61]1)(=[O:9])[C:2]1[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 5922Isonicotinic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1359390885,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinazolin-4(3H)-one

Product 1

HCID 135939100HCID 135939100, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isonicotinic acid (0.083 g, 0.68 mmol) in THF (20 mL) was added HOBt (0.099 g, 0.74 mmol), EDCl (0.141 g, 0.74 mmol), Et3N (0.10 mL, 0.74 mmol) and 5,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinazolin-4(3H)-one (0.250 g, 0.68 mmol). The resulting solution was stirred overnight at room temperature. The solution was concentrated in vacuo and the resulting material was purified by flash chromatography on silica gel, eluting with 10% to 60% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2, to afford the title compound (0.110 g, 34%). 1H NMR (300 MHz, DMSO-d6): δ 11.79 (s, 1H), 8.58-8.79 (m, 2H), 8.12 (d, J=9.0 Hz, 2H), 7.45 (d, J=6.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 2H), 6.69 (s, 1H), 6.47 (s, 1H), 3.64-4.06 (m, 9H), 3.22-3.54 (m, 5H). APCI MS m/z 472 [M+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe resulting material was purified by flash chromatography on silica gel
  3. washeluting with 10% to 60% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2

Sources & evidence

ORD record
ord-9ec187eb57124de4830fd142d572b860
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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