1,2-Dichloroethane → HCID 25226075, compound

HRID 1675943Notes

Reaction equation

HRID 1675943 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[N:11][C:12]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:13]([CH:17]=2)[C:14]([OH:16])=O)[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>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[N:11][C:12]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]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:16])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 79832VeratrylamineHCID 58539048HCID 58539048, compound

Product 1

HCID 25226075HCID 25226075, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-(3-chloro-5-methylphenyl)-2-morpholin-4-ylnicotinic acid (4-2, 2.8 g, 8.41 mmol) and 3,4-dimethoxybenzylamine (6.30 mL, 42.1 mmol) in DCM (42 mL) was added EDC (4.84 g, 25.2 mmol), HOBt (3.87 g, 25.2 mmol) followed by N-methylmorpholine (9.25 mL, 84 mmol) and the system was stirred at 25° C. overnight. The reaction mixture was partitioned between ethyl acetate and water, washed with saturated sodium bicarbonate and dried over magnesium sulfate. The reaction mixture was filtered, concentrated and triturated with diethylether to afford the title compound (4-3) as a bone powder. 1H NMR (400 MHz, CDCl3) δ 8.82 (m, 1H), 8.53 (d, J=2.4 Hz, 1H), 8.49 (d, J=2.4 Hz, 1H), 7.35 (s, 1H), 7.16 (s, 1H), 6.90 (m, 2H), 6.84 (m, 1H), 4.56 (d, J=5.6 Hz, 2H), 3.86 (s, 3H), 3.85 (s, 3H), 3.55 (m, 4H), 3.12 (m, 4H), 2.37(s, 3H). HRMS [M+H] C26H28ClN3O4 calc'd 482.1841, found 482.1847.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated
  6. customtriturated with diethylether

Sources & evidence

ORD record
ord-7041cc86e7e54417b30e14fff19ddba4
Source dataset
uspto-grants-2011_08
Patent number
US08003797B2

Reaction notes

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