1,2-Dichloroethane → Formate

HRID 418328

Reaction equation

HRID 418328 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].[NH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:28]([CH3:30])[CH3:29])=[CH:23][CH:22]=1)=[O:19].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH:13][CH2:14][C:15]1[CH:33]=[CH:32][CH:31]=[C:17]([C:18](=[O:19])[NH:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][N:28]([CH3:29])[CH3:30])=[CH:25][CH:26]=2)[CH:16]=1)=[O:7].[CH:5]([O-:7])=[O:6]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1699823-Chloro-p-anisic acidHCID 44819544HCID 44819544, compound

Product 2

HCID 283FormateYield 423.1%HCID 25054307HCID 25054307, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A reaction vial was charged with 3-chloro-4-methoxybenzoic acid (40 mg, 0.21 mmol), 3-aminomethyl-N-(4-dimethylaminomethyl-phenyl)-benzamide (40 mg, 0.14 mmol), EDC (40 mg, 0.25 mmol) and HOBt (40 mg, 0.29 mmol). DMF (2 mL) was added followed by Hunig's base (0.11 mL, 0.57 mmol). The mixture was stirred at room temperature for 16 h. The product was purified by preparative HPLC using an acetonitrile/water/formic acid gradient providing the title compound as a formate salt (20 mg, 31% yield); MS, electrospray, 452 (M+H).

Workup

  1. customA reaction
  2. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-332f0387552244a0a63ba1c192ea222c
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Linked notes

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