1,2-Dichloroethane → HCID 68666178, compound

HRID 1716822Notes

Reaction equation

HRID 1716822 reaction equation
[N:1]1([CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH3:44][O:45][C:46](=[O:51])[C@H:47]([CH2:49][OH:50])[NH2:48]>CN(C=O)C>[N:1]1([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:48][C@H:47]([C:46]([O:45][CH3:44])=[O:51])[CH2:49][OH:50])=[O:17])=[CH:18][CH:19]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 27354444-(1H-benzimidazol-1-ylmethyl)benzoic acid

Product 1

HCID 68666178HCID 68666178, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 4-[(1H-benzoimidazol-1-yl)methyl]benzoic acid (4 g, 15.87 mmol) in DMF at 0° C. is treated sequentially with EDC (3.6 g, 19 mmol), HOBt (2.5 g, 19 mmol), DIPEA (5.1 g, 39.5 mmol, 2.5 eq) and serine methyl ester hydrochloride (2.9 g, 19 mol), stirred at room temperature overnight and evaporated to dryness. The resultant residue is dissolved in EtOAc and water. The layers are separated and the organic layer is washed successively with 1M HCl, water, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to give the title product in 64% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, DMSO-d6): 8.23-8.26 (m, 2H); 7.9 (s, 2H); 7.87 (d, J=7.6 Hz, 2H); 7.70 (d, J=6 Hz, 1H); 7.33 (m, 3H); 7.20 (m, 2H); 5.54 (s, 2H); 4.90 (t, J=4 Hz, 1H); 4.60 (m, 1H); 3.84-3.90 (m, 2H); 3.70 (s, 3H). LCMS (ESI+) 354 (MH+).

Workup

  1. customevaporated to dryness
  2. dissolutionThe resultant residue is dissolved in EtOAc
  3. customThe layers are separated
  4. washthe organic layer is washed successively with 1M HCl, water, saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d76db4cedc374c2890d60d1bc865e517
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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