1,2-Dichloroethane → 4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-N-(2-diethylamino-ethyl)-benzamide

HRID 1766746Notes

Reaction equation

HRID 1766746 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:4][C:3]=1[O:17][CH2:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH2:41]([N:43]([CH2:47][CH3:48])[CH2:44][CH2:45][NH2:46])[CH3:42]>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:46][CH2:45][CH2:44][N:43]([CH2:47][CH3:48])[CH2:41][CH3:42])=[O:14])=[CH:15][CH:16]=2)=[CH:4][C:3]=1[O:17][CH2:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 60993N,N-DiethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 103181294-[6-Amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-benzoic acid

Product 1

HCID 104355394-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-N-(2-diethylamino-ethyl)-benzamideYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-benzoic acid (50 mg, 0.13 mmol), HOBT (21 mg, 0.156 mmol), and EDC (30 mg, 0.156 mmol) in DMF (2 mL) was added N,N-diethylethylenediamine (0.022 mL, 0.156 mmol). The reaction was stirred at room temperature for 24 hr, then diluted with EtOAc, and partitioned with H2O. The organic was separated and the aqueous was extracted with EtOAc. The organic layers were combined, washed with saturated NaHCO3, and concentrated to dryness under vacuum. The material was purified using column chromatography (silica gel, 99:1 to 95:5 CH2Cl2/MeOH) to give 4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-N-(2-diethylamino-ethyl)-benzamide (45 mg, 72% yield) as a white solid.

Workup

  1. custompartitioned with H2O
  2. customThe organic was separated
  3. extractionthe aqueous was extracted with EtOAc
  4. washwashed with saturated NaHCO3
  5. concentrationconcentrated to dryness under vacuum
  6. customThe material was purified

Sources & evidence

ORD record
ord-5dc3c46ee3cc485faeab0b0d6d77871d
Source dataset
uspto-grants-2007_06
Patent number
US07230098B2

Reaction notes

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