Triethylamine → HCID 57989572, compound

HRID 1095398Notes

Reaction equation

HRID 1095398 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]([CH2:12][CH2:13][S:14][CH3:15])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:24](OC1C=CC([N+]([O-])=O)=CC=1)=[O:25].[CH3:36][N:37]([CH3:46])[C:38](=[O:45])[C@H:39]([C:41]([CH3:44])([CH3:43])[CH3:42])[NH2:40].Cl.CNC>ClCCCl>[CH3:46][N:37]([CH3:36])[C:38]([C@@H:39]([NH:40][C:24]([N:10]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:7]=2[N:8]([CH2:12][CH2:13][S:14][CH3:15])[C:9]1=[O:11])=[O:25])[C:41]([CH3:43])([CH3:42])[CH3:44])=[O:45]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 821294-Nitrophenyl chloroformateHCID 18709502HCID 18709502, compoundHCID 57436051HCID 57436051, compound

Product 1

HCID 57989572HCID 57989572, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 7-methyl-1-[2-(methylthio)ethyl]-1,3-dihydro-2H-benzimidazol-2-one (0.21 g, 0.93 mmol) in 1,2-dichloroethane (5 mL) were added triethylamine (0.43 mL, 3.1 mmol) and 4-nitrophenyl chloroformate (0.23 g, 1.1 mmol) at 0° C. and the mixture was stirred at rt for 4 h. Then to this mixture was added a solution of N,N-dimethyl-tert-leucinamide (ca. 1.4 mmol, prepared according to the procedure described in steps 1 and 2 of example 3 from dimethylamine hydrochloride) in 1,2-dichloroethane (3 mL) at 0° C. and stirred rt. After 14 h, the reaction was quenched by addition of water (50 mL) and extracted with dichloromethane (50 mL×2). The combined organic layers were washed with water (30 mL×4), brine (30 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative TLC eluting with dichloromethane/methanol (10/1) to afford 0.31 g (83%) of the title compound.

Workup

  1. customprepared
  2. customat 0° C.
  3. stirringstirred rt
  4. waitAfter 14 h
  5. customthe reaction was quenched by addition of water (50 mL)
  6. extractionextracted with dichloromethane (50 mL×2)
  7. washThe combined organic layers were washed with water (30 mL×4), brine (30 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by preparative TLC
  12. washeluting with dichloromethane/methanol (10/1)

Sources & evidence

ORD record
ord-93d37480e0a7432990a4151e8b09d47d
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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