1,2-Dichloroethane → Formate

HRID 418327Notes

Reaction equation

HRID 418327 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])=[O:7].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[CH3:45][N:46]([CH2:48][C:49]1[CH:50]=[C:51]([NH2:55])[CH:52]=[CH:53][CH:54]=1)[CH3:47]>CN(C=O)C>[CH3:47][N:46]([CH2:48][C:49]1[CH:50]=[C:51]([NH:55][C:13]([C:12]2[CH:11]=[C:10]([CH:18]=[CH:17][CH:16]=2)[CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:15])[CH:52]=[CH:53][CH:54]=1)[CH3:45].[CH:13]([O-:15])=[O:14]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 992943-amino-N,N-dimethylbenzylamineHCID 448195433-[(3,4-Dimethoxy-benzoylamino)-methyl]-benzoic acid

Product 2

HCID 283FormateYield 1,399.3%HCID 25054030N-[3-(3-dimethylaminomethyl-phenylcarbamoyl)-benzyl]-3,4-dimethoxy-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-[(3,4-Dimethoxy-benzoylamino)-methyl]-benzoic acid (40 mg, 0.127 mmol), prepared as described in Example 8, was combined with EDC (38.3 mg, 0.2 mmol) and HOBt (24.3 mg, 0.18 mmol) in a reaction vial, and DMF (1 mL) was added followed by N-methylmorpholine (0.025 mL, 0.22 mmol). The resulting mixture was agitated for 1 h, then 3-dimethylaminomethyl-phenylamine (25.5 mg, 0.17 mmol) was added as a solution in DMF (0.5 mL), and the resulting mixture was agitated overnight. The product was purified directly by preparative HPLC using an acetonitrile/water/formic acid gradient providing the title compound as a formate salt (40 mg, 70% yield), MS analysis electrospray, 448 (M+H).

Workup

  1. additionwas added
  2. stirringthe resulting mixture was agitated overnight
  3. customThe product was purified directly by preparative HPLC

Sources & evidence

ORD record
ord-78ba5dfa3fb841de96e969a04a7d9213
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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