1,2-Dichloroethane → HCID 24811988, compound

HRID 1945429Notes

Reaction equation

HRID 1945429 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.C[O:15]C(=O)C1C=C(N)C=NC=1.[CH3:25][CH2:26][N:27]([CH:31]([CH3:33])C)[CH:28]([CH3:30])C.C(Cl)CCl.[CH:38]1[CH:39]=[CH:40][C:41]2N(O)N=[N:44][C:42]=2[CH:43]=1.[CH3:48][N:49]([CH:51]=[O:52])C>>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH:44][C:42]1[CH:41]=[C:40]([CH:39]=[CH:38][CH:43]=1)[C:51]([NH:49][CH2:48][CH2:33][CH2:31][N:27]1[CH2:26][CH2:25][O:15][CH2:30][CH2:28]1)=[O:52])=[O:8]

Participants

7

Reactant 6

HCID 111,2-DichloroethaneHCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1514432Methyl 5-aminopyridine-3-carboxylate

Product 1

HCID 24811988HCID 24811988, compoundYield 60%

Procedure

To solution of (2,4-dichloro-phenoxy)acetic acid (192.7 mg, 0.87 mmol), 5-amino nicotinic acid methyl ester (200 mg, 1.31 mmol) and DIPEA (169.8 mg, 1.31 mmol) in DMF 5 mL was added EDC (252 mg, 1.31 mmol) and HOBt (177.62 mg, 1.31 mmol) at room temperature. Reaction mixture was stirred at room temperature, poured onto ice cold water, extracted with ethyl acetate, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:9˜1:1) to give 3-[2-(2,4-dichloro-phenoxy)-acetylamino]-N-(3-morpholine-4-yl-propyl)-benzamide as a colorless solid (0.185 g, 60% yield).

Workup

  1. customReaction mixture
  2. additionpoured onto ice cold water
  3. extractionextracted with ethyl acetate
  4. washsequentially washed with aqueous sodium bicarbonate, brine and water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:9˜1:1)

Sources & evidence

ORD record
ord-6769dae3f54942f58fce8dbf89302018
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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