Tetraethyl orthocarbonate → HCID 117601189, compound

HRID 1773728Notes

Reaction equation

HRID 1773728 reaction equation
[NH2:1][C:2]1[C:13]([NH2:14])=[CH:12][C:11]([C:15]2[C:16]([CH3:21])=[N:17][O:18][C:19]=2[CH3:20])=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5].[CH2:22]([O:24][C:25](OCC)(OCC)OCC)[CH3:23]>CC(O)=O>[CH3:21][C:16]1[C:15]([C:11]2[CH:10]=[C:3]([C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5])[C:2]3[N:1]=[C:25]([O:24][CH2:22][CH3:23])[NH:14][C:13]=3[CH:12]=2)=[C:19]([CH3:20])[O:18][N:17]=1

Participants

4

Reactant 2

HCID 66213Tetraethyl orthocarbonateHCID 117601942HCID 117601942, compound

Product 1

HCID 117601189HCID 117601189, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,3-diamino-5-(3,5-dimethylisoxazol-4-yl)-N-methoxy-N-methylbenzamide (25 g, 0.086 mol) was dissolved in a 1:1 mixture (32 mL total) of tetraethylorthocarbonate and AcOH and allowed to stir under air at room temperature for 1.5 hr. The reaction mixture was concentrated in vacuo at room temperature and the crude residue was dissolved in EtOAc. The solution was washed three times with bicarb, once with water, and organic layer was concentrated in vacuo to give 6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-N-methoxy-N-methyl-1H-benzo[d]imidazole-4-carboxamide as a dark oil. Crude material was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo at room temperature
  2. dissolutionthe crude residue was dissolved in EtOAc
  3. washThe solution was washed three times with bicarb
  4. concentrationonce with water, and organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-06bfc8e479124f408788d59b531870b4
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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