1,2-Dichloroethane → Methyl {3-[2-(dimethylamino)-2-oxoethyl]-5,7-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}acetate

HRID 1921180Notes

Reaction equation

HRID 1921180 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]1[C:9]2[C:10]([CH3:15])=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=2[N:7]([CH2:16][C:17]([OH:19])=O)[C:6]1=[O:20].Cl.[CH3:23][NH:24][CH3:25].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:23][N:24]([CH3:25])[C:17](=[O:19])[CH2:16][N:7]1[C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2[N:5]([CH2:4][C:3]([O:2][CH3:1])=[O:21])[C:6]1=[O:20]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 18449372[3-(2-Methoxy-2-oxoethyl)-4,6-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetic acid2×

Product 1

HCID 86619733Methyl {3-[2-(dimethylamino)-2-oxoethyl]-5,7-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [3-(2-methoxy-2-oxoethyl)-4,6-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetic acid (Intermediate 9) (305 mg, 1.04 mmol), N,N-dimethylamine hydrochloride (128 mg, 1.60 mmol), EDC (300 mg, 1.60 mmol), HOBT (240 mg, 1.60 mmol), and N,N-diisopropylethylamine (0.909 mL, 5.20 mmol) were stirred for 16 h at ambient temperature in DMF (3 mL): The mixture was partitioned between CH2Cl2 (10 mL) and saturated NaHCO3 (10 mL) and the organic layer was dried over Na2SO4, filtered, and concentrated to give the compound. MS: m/z=320 (M+1).

Workup

  1. customThe mixture was partitioned between CH2Cl2 (10 mL) and saturated NaHCO3 (10 mL)
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the compound

Sources & evidence

ORD record
ord-06f7536aa93343d0a45c56a890db2a2b
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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