Triethylamine → HCID 178513788, compound

HRID 391633Notes

Reaction equation

HRID 391633 reaction equation
[NH2:1]/[C:2](/[C:17]#[N:18])=[C:3](\[NH:6][C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]1)=[O:8])/[C:4]#[N:5].O[C@@H]1C[CH2:24][C@H:23]([C:26](O)=O)[CH2:22][CH2:21]1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.[O-][Mn](=O)(=O)=O.[K+].N/C(/C#N)=C(\N)/C#N.C([O:70][CH2:71][CH3:72])(=O)C>C1(C)C=CC=CC=1.C(#N)C>[OH:16][C@H:13]1[CH2:14][CH2:15][C@H:10]([N:9]2[C:7](=[O:8])[NH:6][C:3]3[C:4]2=[N:5][C:26]([C:23]2[CH:22]=[CH:21][CH:72]=[C:71]([OH:70])[CH:24]=2)=[N:1][C:2]=3[C:17]([NH2:18])=[O:43])[CH2:11][CH2:12]1

Participants

10

Reactant 7

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 516875Potassium PermanganateHCID 2723951DiaminomaleonitrileHCID 178511349HCID 178511349, compoundHCID 178525779HCID 178525779, compound

Product 1

HCID 178513788HCID 178513788, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

1-((Z)-2-Amino-1,2-dicyanovinyl)-3-(trans-4-hydroxycyclohexyl)urea. cis-4-Hydroxycyclohexane carboxylic acid (2.0 g, 13.87 mmol), triethylamine (1.40 g, 13.87 mmol) and diphenylphosphorylazide (3.81 g, 13.87 mmol) were combined in toluene and stirred at room temperature. The reaction was monitored via thin layer chromatography (50% ethyl acetate in hexanes, KMnO4 stain). After 30 min the solution was condensed under reduced pressure and the oil diluted with acetonitrile (30 mL) followed by the addition of diaminomaleonitrile (1.57 g, 14.56 mmol). The solution was heated to 65° C. for 16 h. The solution was condensed under reduced pressure and partitioned between water and ethyl acetate (3×), organics combined, dried over magnesium sulfate, filtered and solvent removed to afford the crude product. The crude oil was purified using Biotage silica gel chromatography (70-100% ethyl acetate in hexanes followed by 10% methanol in ethyl acetate) to afford the title compound (1.90 g, 37%). MS (ESI) m/z 250.1 [M+1]+.

Workup

  1. customcondensed under reduced pressure
  2. temperatureThe solution was heated to 65° C. for 16 h
  3. customcondensed under reduced pressure
  4. custompartitioned between water and ethyl acetate (3×)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customsolvent removed
  8. customto afford the crude product
  9. customThe crude oil was purified

Sources & evidence

ORD record
ord-22d80733645b44dd91dcae469561285b
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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