1,2-Dichloroethane → HCID 25224951, compound

HRID 1675939Notes

Reaction equation

HRID 1675939 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[N:11][C:12]([C:18]3[CH:19]=[N:20][N:21]([CH3:23])[CH:22]=3)=[C:13]([CH:17]=2)[C:14](O)=[O:15])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:29][NH2:30].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[N:11][C:12]([C:18]3[CH:19]=[N:20][N:21]([CH3:23])[CH:22]=3)=[C:13]([CH:17]=2)[C:14]([NH:30][CH2:29][C:28]2[CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:26]([O:25][CH3:24])[CH:27]=2)=[O:15])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 79832VeratrylamineHCID 58539043HCID 58539043, compound

Product 1

HCID 25224951HCID 25224951, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-(3-chloro-5-methylphenyl)-2-(1-methyl-1H-pyrazol-4-yl)nicotinic acid (2-2, 0.050 g, 0.153 mmol) and 3,4-dimethoxybenzylamine (0.099 g, 0.595 mmol) in dimethylformamide (1 mL) was added EDC (0.132 g, 0.686 mmol), HOBt (0.105 g, 0.686 mmol) followed by N-methylmorpholine (0.250 mL, 2.28 mmol) and the system was stirred at 25° C. overnight. The reaction mixture was partitioned between ethyl acetate and water, washed with saturated sodium carbonate and dried over magnesium sulfate. The reaction mixture was filtered and purified via normal phase chromatography (0→5% MeOH in DCM) to afford the title compound (2-3) as a bone-colored powder. 1H NMR (500 MHz, CDCl3) δ 8.81 (d, J=2.5 Hz, 1H), 7.99 (s, 1H), 7.92 (d, J=2.5 Hz, 1H), 7.78 (s, 1H), 7.38 (s, 1H), 7.28 (m, 2H), 7.23 (s, 1H), 6.84 (s, 2H), 6.06 (m, 1H), 4.55 (d, J=6 Hz, 2H), 3.88(s, 3H), 3.87(s, 3H), 3.86(s, 3H), 2.42 (s, 3H). HRMS [M+H] C26H25ClN4O3 calc'd 477.1688, found 477.1682.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washwashed with saturated sodium carbonate
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe reaction mixture was filtered
  5. custompurified via normal phase chromatography (0→5% MeOH in DCM)

Sources & evidence

ORD record
ord-e69489268429418f8f1df457fb983b47
Source dataset
uspto-grants-2011_08
Patent number
US08003797B2

Reaction notes

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