1,2-Benzenediamine, N1-ethyl- → HCID 11856842, compound

HRID 1162919Notes

Reaction equation

HRID 1162919 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([CH:20](OCC)OCC)[NH:15][C:16]3=[O:19])=[CH:11][CH:10]=2)[CH2:4]1.[CH2:27]([NH:29][C:30]1[C:31]([NH2:36])=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH3:28]>>[CH2:27]([N:29]1[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[N:36]=[C:20]1[C:14]1[NH:15][C:16](=[O:19])[C:17]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([N:5]1[CH2:4][C@H:3]([CH2:2][OH:1])[O:7][C:6]1=[O:8])[CH:18]=2)[CH3:28]

Participants

3

Reactant 2

HCID 902751,2-Benzenediamine, N1-ethyl-HCID 57557962HCID 57557962, compound

Product 1

HCID 11856842HCID 11856842, compoundYield 74.2%

Procedure

Purified water (0.01 ml) and TFA (0.01 ml) were added to a dichloromethane solution that contained the 7-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-diethoxymethyl-2H-isoquinolin-1-one (3.3 mg, 0.009 mmol) prepared in step C. The obtained mixture was left at a room temperature for 30 minutes, and the reaction solution was concentrated. The obtained yellow solid and an ethanol solution that contained N-ethyl-1,2-benzenediamine (1.2 mg, 0.009 mmol), which was a known compound described in a publication (Leicester Polytech; Synthetic Communications, vol. 19(7-8), p. 1381, (1989)), were heated to reflux for 17 hours. Thereafter, the reaction solution was concentrated. The obtained residue was purified by preparative silica gel TLC (dichloromethane:methanol=20:1), so as to obtain 3-(1-ethyl-1H-benzoimidazol-2-yl)-7-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-2H-isoquinolin-1-one (2.7 mg, yield: 74%) in the form of a yellow solid.

Workup

  1. customPurified water (0.01 ml) and TFA (0.01 ml)
  2. additionwere added to a dichloromethane solution that
  3. concentrationthe reaction solution was concentrated
  4. temperaturewere heated
  5. temperatureto reflux for 17 hours
  6. concentrationThereafter, the reaction solution was concentrated
  7. customThe obtained residue was purified by preparative silica gel TLC (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-5062ef1ab4db41f6b8e4bf80f79a0273
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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