Triethylamine → HCID 135939101, compound

HRID 591626Notes

Reaction equation

HRID 591626 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(CC)CC.[CH3:38][O:39][C:40]1[CH:49]=[C:48]([O:50][CH3:51])[CH:47]=[C:46]2[C:41]=1[C:42](=[O:64])[NH:43][C:44]([C:52]1[CH:57]=[CH:56][C:55]([N:58]3[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]3)=[CH:54][CH:53]=1)=[N:45]2>C1COCC1>[CH3:38][O:39][C:40]1[CH:49]=[C:48]([O:50][CH3:51])[CH:47]=[C:46]2[C:41]=1[C:42](=[O:64])[NH:43][C:44]([C:52]1[CH:57]=[CH:56][C:55]([N:58]3[CH2:59][CH2:60][N:61]([C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[O:8])[CH2:62][CH2:63]3)=[CH:54][CH:53]=1)=[N:45]2

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 107002-Thiophenecarboxylic acidHCID 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 135939101HCID 135939101, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-thiophenecarboxylic acid (0.087 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 at room temperature for 4 hours. The solution was concentrated in vacuo. The material was purified by flash chromatography, eluting with 0% to 50% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2, to afford the title compound (0.100 g, 30%). 1H NMR (300 MHz, DMSO-d6): δ 11.78 (s, 1H), 8.12 (d, J=9.0 Hz, 2H), 7.75-7.84 (m, 1H), 7.46-7.53 (m, 1H), 7.12-7.20 (m, 1H), 7.03 (d, J=9.1 Hz, 2H), 6.69 (d, J=2.3 Hz, 1H), 6.47 (d, J=2.3 Hz, 1H), 3.88 (s, 3H), 3.83 (s, 3H), 3.74-3.92 (m, 4H), 3.37-3.49 (m, 4H). APCI MS m/z 477 [M+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customThe material was purified by flash chromatography
  3. washeluting with 0% to 50% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2

Sources & evidence

ORD record
ord-4243724e15654e6798104356fcd1d83e
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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